Over on the Outliner Software forum, Ecco Pro often comes up as a benchmark. Much nostalgia for it there
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What about using a table of contents? If you create a header for each conversation that contains the pertinent details (e.g. 2022-08-18 - Acme, Inc. - Wyle E. Coyote - phone call re: TNT shipment), then all you’d have to do is scan the TOC to find the section you’re looking for. Click on it, and you’re there.
The only caveat is that you would have to rebuild the TOC every time you update the document, but that’s just a few clicks.
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You could re-build the TOC. Nevertheless, with the “headers view” (or whatever it’s called) in the sidebar, you wouldn’t even need to use the TOC. You could just use that as an automatic TOC and jump to the sections by clicking on them.
Not to suggest more apps but . . .
If you’re making a lot of calls or having meetings and taking notes on those, you may want to look at
There are Mac and iOS versions (separate purchases). Tags can be used to group contacts together. Logs can be copied or exported (including as a PDF).
So far it’s worked really well for me.
I’m also a fan of the previously mentioned Curio. In case you haven’t seen it there is a blog entry from 2012 on a lawyer using Curio as a lawyer’s briefcase.
You may have also seen this 2014 video by a trial lawyer on how he uses Circus Ponies Notebook in trial. It’s about an hour long. Unfortunately, Circus Ponies Notebook is no longer being updated. Still, there might be some useful ideas.
If you want to go with the notebook metaphor on MacOS Monterey, NoteTaker by AquaMinds may be the closest successor.
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Just for the curious: Circus Ponies and Notetaker were both forks of an original app produced for the Next machines. The team split and CPN and Notetaker were the results. They had a lot in common. It seems as well that OneNote was inspired by the original app.
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I saw that the pricing for Lit Suite is $399.99/year (with early subscriber discount)
As for NoteTaker, I have used it for some personal projects as a sort of focus tool. I can’t seem to customize it as much as I’d like. If there’s a way to change the tab colors or use my own notebook cover designs I can’t figure it out.
My suggestion is DEVONthink 3. However I am very much not an attorney if I can put it that way and I know enough to know my own workflow would not work for an attorney. However DEVONthink 3 is an amazing app and the learning curve should not intimidate because you don’t need to know ALL of it or MOST of it, you can use it, as I did at first, on a just open and go basis. Use the AI and search functions from the get go though if you try it.
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OP UPDATE
For entering all my case notes and later be able to search for tags such as incident, injury, treatment, insurance, settlement discussions, etc. (I abbreviate these tags), I tried the following:
- Logseq
- OneNote
- Workflowy
- Word
- Nimbus Note
- Curio
- and my ultimate choice, see below (spoiler: it’s Obsidian)
I also investigated Craft and Notion. Every one of the apps I tried are excellent in their own ways. The one that came closest was Nimbus Note. But where they all didn’t work for me is the search ability. I want to be able to search for specific tags for a specific case and see the sections of my notes that contain them. And I still can’t. But I think I’ll be able to in the future, with my choice:
Obsidian. I’ve started entering notes for all my new cases into it. It’s not as polished as most of the other apps, even with downloaded, community themes. And I don’t yet have a good search ability implemented. But it keeps my notes in a format that can be read by other apps and be easily accessed and moved, and I think its devs and its large developer community will make entering and searching my notes increasingly easier in the future.
Thanks for all your replies and suggestions, above!
My next project is a data bucket that will be the repository of all my non-case related content such as court cases, statutes, articles, web pages, webinar notes, forms, etc. And perhaps it will also search my case notes, as well. I’m going to make another topic thread for this (hopefully the subject hasn’t been played out too much recently already). 
Devonthink will handles your case notes/tags/searching well. It can also serve as your “data bucket.”
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I tried DevonThink’s 30-day (generous, full-featured) trial. I would prefer to index than import, but I’m not 100% on board with DT’s indexing and its UI. But it’s widely-used and well-supported, and is my frontrunner. I’m also looking at Foxtrot Professional Search and EagleFiler.
i am curious on why you prefer indexing the pointers to files instead of importing?
I doubt he will want to index for legal work.
Legal case usually requires archiving documents for an extended time… If you import to a DT3 database, then it is self-contained; there is no risk of losing things when an external volume/folder is moved or deleted.
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I could be misunderstanding the issues. I have about 50GB that I want to be able to search. I will chiefly use this for searching my personal legal database of the types I mentioned (and also Outlook emails that I import or index). The client files and notes will always be in their current folder structure so I and others can easily and directly access them.
I like the idea of indexes because I’m still able to browse and access the files from any device. But I had two glitches with indexes in my trial. One was that I didn’t need my wife’s Dropbox subfolder in the index, so I removed it from the index not realizing that it also deleted it from my disk and from Dropbox itself. Fortunately, I restored it in a few minutes using Dropbox’s website, but it should have warned me before letting me do that. Second, I searched for a file that I indexed and it found it, but when I tried to view it, it was no longer there because I had moved it. (I also found the UI to be busy and complex, but I’m sure I can adjust that to suit my use.)
It’s important to me that the databases be quickly synched between my upcoming desktop Mac and my MBP, which DT says it does well.
I know I can keep a separate index for the client files and client notes, and import everything else. This is what will most likely happen unless another app is better suited to this.