I want to be able to take notes as an outline with DTP, but can’t fix the order of numerals (i.e the numbers and letters use for the outline headers). I say “fix,” because although I can get this to work for a single case, I’m looking to use the same scheme in the nth case.
Specifically, I want the order to be:
I. Roman Number (uppercase)
A. Uppercase letter
1. “Arabic” numbers
a. Lowercase letter
i. Roman number (lower case)
In DTP, if I start with uppercase Roman numbers, a hard return + tab produces a dash " - ". I then have to change the dash to an uppercase letter, A. Another har return + tab produces yet another dash, so I have to edit to lowercase. This I have to do every time I want to make an outline.
Is there no way to force the order of numerals to the above so that this is the default numeral system? It’s a rather common outline scheme, and I find that I avoid DTP anytime I see that an outline is required for note taking.
DEVONthink uses the List structure of TextEdit. That’s great for simple bullet lists. I suppose, with a great deal of patience and manual labor I could force a highly structured outline using the List options. I think my life is simpler and more productive if I decide not to do that. 
I use rough outlines in many of my notes. Long ago, I had an outliner application, but found I didn’t make much use of it to make structured outlines, after all. Some people work that way, others don’t.
I think that there are some outliner applications that can save their structure in rich text. If so, you might use such an application to create highly structured outlines and save their output to your database. Of course, they could best be edited under their parent application, as the Cocoa text code used in DEVONthink (essentially, TextEdit) would not be easy to use on such a structured document.
Useful information. If you have any such apps in mind, feel free to post them here or send me a private msg.
Thanks
OmniOutliner is pretty much the undisputed king of outliners for OS X, so far as I can tell. It’s a very good app. It’s quite expensive for the Pro edition, but if you outline a lot I’m sure it’d be justified over time. It exports very, very well to several different formats. It also has a quite good Quicklook plugin, so you can import the document into DTP and pretty much do anything but edit (you can expand/collapse branches, etc). You can’t copy text or convert it to text, but if you need to edit it or get the text you can just open it externally.