Cloud Outliner finally released version 2 for OS X, which syncs with the iOS version via iCloud.

Workflowy and Dynalist are nicer desktop outliners, but neither has a decent iOS app. If you primarily work on iOS this seems worth looking at, since the iOS native app is much easier to use on the iPhone than the webview-only options offered by these others.

https://itunes.apple.com/us/app/cloud-outliner-2-pro-outline/id1024917449?mt=12

Despite lacking a lot of features, but it does allow you to customize the shortcuts as you like, and you can import/export OPML files with other outliners.

Putting the app through its paces, I find that it is very slow, frequently giving me a spinning wheel and becoming unresponsive. I hope they can fix these performance issues, otherwise it is not much use for any real work...

Thank you for alerting us about this new version of Cloud Outliner. Being a fan of the iPad app, I had to give this a whirl. I haven't had the hang up issues you describe, but the outline I created was not very big.

What I did find disappointing is the inline note feature. Creating and editing a note is awkward. It works, but I felt like I was fumbling around a lot. The cursor didn't seem to respond well to the track pad. I had to navigate around in the note with my arrow keys to get to the point I wanted to go.

And, as you said, it isn't very feature rich for a desktop outliner. Presumably features will be added and issues like the one I had with the notes will be ironed out in the future.

Steve Z.

After more use I'm even more dissatisfied with Cloud Outliner 2 for OS X. I've had sync failures, crashes, etc. on a daily basis. I really *want* this to work because I want an iOS-first solution to outlining that also syncs with the desktop and this is the only one I know of, but I can't consider this release to be anything other than a poorly tested beta app.

Luhmann wrote:

After more use I'm even more dissatisfied with Cloud Outliner 2 for OS
X. I've had sync failures, crashes, etc. on a daily basis. I really
*want* this to work because I want an iOS-first solution to outlining
that also syncs with the desktop and this is the only one I know of, but
I can't consider this release to be anything other than a poorly tested
beta app.

Can't OmniOutliner do all of that?

Good question. I used OmniOutliner years ago (before there was an app store) and found it very clunky with lots of non-outliner features (it seemed more like a spreadsheet program). A few years ago I looked at it again but didn't buy it at the time because there was no sync solution. I don't know what the situation is now. I see they just released a new version, but it is very expensive and there are quite a lot of negative reviews for such a costly program. What are people's experiences with it on this forum? How is sync? How is it for simple outlining on the the iPad or iPhone?

According to the reviews for the OS X version of Omni Outliner it is very crash prone, so it doesn't sound like spending all that money would solve the crashing problems I'm facing with Cloud Outliner.

Luhmann wrote:

How is it for simple outlining on the the
iPad or iPhone?

For simple outlining on iOS you could try CarbonFin (http://carbonfin.com/index.html It doesn't have a desktop app, but it syncs with a web app (https://cfoutliner.appspot.com/ that you can access via a browser (and download the files as OPML). Apparently its files can also be accessed by desktop outliners via Dropbox as OPML.

I have OmniOutliner installed on both my MacBooks and on my iPad Air. I can't say that I use it extensively, but I do use it. I haven't experienced any crashes, but my outlines are not big, sprawling things. Building a simple outline on the iPad is pretty standard. It's when you want to make use of the columns that it starts to feel a bit clunky, though I'm not sure there's a way around that on a device like the iPad.

To me the main drawback is that they encourage you to use their proprietary sync-service, OmniSync. This is free, but it isn't as simple as Dropbox or even iCloud. They say their service is better because the others are not set up to handle the package files used by OmniOutliner (and their other apps, OmniFocus, etc.).

All in all, I haven't found it overly inviting to use OO, though I do for some specific outlines, where the features of OO are required, and it is perfectly functional for those purposes. For example, planning the events lined up for the historic site where I volunteer. The columns and inline notes are helpful for planning. Then, once the schedule is set, I can create a good-looking PDF of the schedule for distribution.

Steve Z.

There's still a dearth of really good outliners for MacOS and iOS. There are excellent outliners for one or the other, but very few for both. Cloud Outliner 2 is okay, but clearly giving some people problems. OmniOutliner isn't as good as it purports to be: I've found that it slows down drastically as outlines become longer, especially on iOS. The fact that Carbonfin Outliner is still one of the more capable products is a bit bloody sad.

There are excellent cross-platform writing and note-taking apps (effectively two/three-pane outliners) that are extremely capable; I won't bother to list them here because there are so many. But none of them are outliners in the sense of one-pane, folding outliners like Workflowy (which would be wonderful if it wasn't web-bound).

There are also difficult-to-categorise notebook managers like OneNote, Outline+ and Growly Notes that are not really outliners (well, okay, the desktop version of OneNote is a folding outliner, but none of the iOS versions does folding) but are still powerful.

Funnily enough, the most capable outliners are currently task managers. The new version of Todoist is an extremely capable outliner - although it's optimised for task management, it could, at a pinch, serve as an outliner (complete with tags etc.) Two others worth mentioning are The Hit List (now available on iPad as well as iPhone, plus Mac OS; uses tags and contexts, as well as folders, folding etc.) and Pagico. Oh, and OmniFocus, I suppose, although I find it seriously clunky on iOS. In some ways, it's amusing: for a long time there was much moaning about the fact that task managers weren't exploiting the benefits of folding - now they're the leading exponent of the model.

So come on, Robin! When are we going to see OutlineEdit as an iOS app? For that matter, when are we going to see the spectacular Tree 2 or Outlinely as iOS apps? (Having said that, Glam Development, developers of Outlinely, appear to have disappeared). Ah well, we can but hope...

You've summed it up perfectly, Bill.

One suggestion that may be unpalatable for many, but might also work is to rely instead on a mind-map-style program. Applications like Simple Mind and iThoughts have done a great job, I think, bridging the iOS and OSx worlds. (Why it would be easier to build workable diagramming applications on both platforms than it is to build outliners is a mystery, at least to me.) You can export them to OPML to import into a dedicated outline application, if need be.

Anyway, that is just a consideration.

Steve Z.

i think the shortage is due to the fact that people buy 1000$ phones but then expect every app to be 1$ (of which 30% go to Apple and because you can only sell iOS apps on the AppStore there is no way around it). nobody can make a living doing that – this is why a lot of applications disappear suddenly. at the same time outliners are not sexy enough to attract venture capital (unlike task managers). all in all this seems to leave power users unsatisfied (because they cannot use the abilities of their 1000$ phones, but casual users very happy because they get a lot of new apps for 1$ all the time. it's a vicious cycle.

MadaboutDana wrote:

The
fact that Carbonfin Outliner is still one of the more capable products
is a bit bloody sad.

On the other hand how sophisticated or complex does a tablet or mobile phone outlining app really need to be? Outlining in itself is quite a simple and straightforward concept and activity.

I don't use iOS apps for outlining any more (other than glancing at my WorkFlowy app once in a while on my iPod Touch), but could it be that these phone and tablet apps get too complicated for their own good, and then leave users inevitably dissatisfied?

I do wish though that the WorkFlowy app in iOS and Android was more straightforward to use.

Hasn't it almost always been the case that the best outliners seem to be task managers? Thinking all the way back to Ecco Pro, here.

Anyway, I feel like this discussion more highlights the value of open file formats. I don't think passing plain text or OPML files back and forth between apps via Dropbox (though, I wish iOS developers would consider other sync options outside just one cloud provider and iCloud) is the worst thing in the world.

I also agree with Dr. Andus, how complicated does a tablet-based outliner need to be? This reminds me, I should probably play with iThoughts some more. I never really got into the mind map format, but perhaps it's a better way of working on tablet? It does export to OPML, so I could pull something made in there into a "proper" outliner for further work.

I agree about open file formats - very much, in fact.

But not so sure about "complicated". I don't need complicated, but I do look for a few things:
- modest rich text support (bold, italics, ideally underline, strikethrough, ideally colours)
- tags (or contexts)
- notes are nice (but not essential)

For me, those are the basic things required in a competent outliner. Why rich text? Because in a large/complex outline, it helps to be able to highlight/emphasize certain things so they immediately spring to the eye. That's why I quite like Todoist, actually (although I'm currently using Trello - which supports Markdown, I'm gratified to find, plus team sharing).

I don't give a monkey's about file attachments etc., but can see why some people might like them.

Columns are always cool, too (or horizontal trees, a la Tree 2 or Gingko). But hey, that's getting "complicated"!

Stephen Zeoli wrote:

I have OmniOutliner installed on both my MacBooks and on my iPad Air. I
can't say that I use it extensively, but I do use it. I haven't
experienced any crashes, but my outlines are not big, sprawling things.
Building a simple outline on the iPad is pretty standard. It's when you
want to make use of the columns that it starts to feel a bit clunky,
though I'm not sure there's a way around that on a device like the iPad.

To me the main drawback is that they encourage you to use their
proprietary sync-service, OmniSync. This is free, but it isn't as simple
as Dropbox or even iCloud. They say their service is better because the
others are not set up to handle the package files used by OmniOutliner
(and their other apps, OmniFocus, etc.).

All in all, I haven't found it overly inviting to use OO, though I do
for some specific outlines, where the features of OO are required, and
it is perfectly functional for those purposes. For example, planning the
events lined up for the historic site where I volunteer. The columns and
inline notes are helpful for planning. Then, once the schedule is set, I
can create a good-looking PDF of the schedule for distribution.

Steve Z.

My main beef with OO is that it still, on Version 4 now, doesn't offer "clones". I seem to remember that you've criticised it on these grounds in the past, Steve; there've certainly been plenty of posts in the Omni forums calling for this feature. I too find the columns and inline notes helpful, but the absence of clones in my work outlining writing that "tells 'em what you're gonna tell 'em, tells 'em and then tells 'em what you've told 'em" (i.e. it requires a degree of repetition) triggers extra work that software surely ought to be able to handle with ease. I seem to remember that a decade or so ago, Brainstorm offered clones!

MadaboutDana wrote:

Thefact that Carbonfin Outliner is still one of the more capable products
is a bit bloody sad.

I completely forgot I had Carbonfin. After firing it up for the first time in years last night, I realized why. I agree, it is pretty sad. Though, I think part of the problem stems from the lack of a Tab key or arrow keys and all the ways one would normally interact with an outline. For some reason, it doesn't seem like anyone has bothered to try to translate the UI to a touch interface. Like, swipe right to indent or something. Is there anything that operates like that?

It's also really cluttered which makes it less useful even for just reading an outline on the go. Carbonfin also suffers from the problem I have with a lot of outliners in that it can't seem to decide if it's a task management app or a writing app, which contributes to the clutter.

iThoughts HD, however, is pretty good despite being a mind map and not an outline app. I did successfully make a quick map, export it as OPML and with a brief stop over in Pandoc, had it open on my PC in Org-Mode where I could do some real writing.

I guess none of this helps much if you're trying to use your iPad as a laptop replacement, but I think this is a decent workflow.

CarbonFin is still a really good single pane outliner. And it has several ways to move data to other programs.

Likewise, SimpleMind and iThoughts are excellent mindmap programs, which also move data reliably.

As is so often the case, one's satisfaction with software comes down to what one needs to do with it. My user cases are pretty narrow: I'm giving a talk (mind maps are best) or I'm writing something (I want outlining, collapsing, expanding, moving by section). SimpleMind is a good cross-platform tool, as is Xmind, for talks. For writing, markdown (org-mode or Editorial) does the trick.

Your mentions of mind-mapping apps have reminded me of an app that is iOS/Mac-compatible, and used to be a really good halfway house between mindmapping and outlining: MagicalPad

Alas, in the jump to MacOS, it became a steroid-bloated monster that simply isn't any fun to use any more, despite a plethora of "cool" features. The early iOS versions used to be very slim, neat and clever.

I'd love to see a slimmed-down version of MagicalPad out in the wild. As it is, I tend to open it, wince sharply, and close it again...

MadaboutDana wrote:

There's still a dearth of really good outliners for MacOS and iOS. There
are excellent outliners for one or the other, but very few for both.

Indeed. I have a thought about why that is.

The key feature of an excellent outliner is the user interaction paradigm. At the very least one needs to be able to quickly indent, outdent, select, and move items around. But there is much more than that as well. An outliner is a text manipulation tool whose functions differ from those of a word processor. The user needs to be able to split paragraphs into separate items, merge multiple paragraphs, move items from one list to another, duplicate lists, etc. A good outliner makes all of these actions so quick and easy that you don't even have to stop and think about it.

Now, here's the rub: the ideal user interaction interface for all of these tasks will be very different on a touch screen interface than it is on a keyboard. Some developers, like those behind Workflowy, seem to have really thought about how to work well with a keyboard, but not really put a lot of thought into how to work with a touch screen. I have not seen any outliner that works as well on the iOS interface as Workflowy works on a desktop.

It frustrates me because the app store is full of hundreds of copy-cat task managers, "minimalist" markdown editors, and even mind mappers, but the outlining category is still very weak, especially on the phone. There are lots of great ideas out there, with Cloud Outliner perhaps being the best so far, but none of them are as well executed. (Tree seems like it would be particularly well suited to iOS, but the developer doesn't seem interested.)

Another problem is sync. Even with iCloud and Dropbox, it seems hard to implement cross platform sync well, and so any developer who wanted a cross-platform solution would also need to become an expert on sync which makes the whole project quite daunting. Still, I'd be willing to pay good money for a top-of-the-line cross platform outliner. Too bad that Omni Outliner doesn't seem like it's that solution...

PS: Mind Mapping is IMHO completely useless for dealing with large amounts of text. I have yet to see a Mind Mapper which can handle more than short phrases in a way which makes it easy to see what you are working on.

Cloud Outliner 2 released a new update for the Mac. I thought I'd delete some of my existing outlines and re-import from Workflowy to try it again, but the app just hangs and does nothing when I try to delete a folder of outlines. Still too buggy for actual use...