I kept trialing alternatives like VimWiki, Joplin and Logseq, but everything else is even quirkier. Org-mode is about the only thing that seemed really competitive, but since I’m not an emacs person there’s a big ramp there for me. Plus, as with most of the alternatives, that loses Markdown compatibility entirely.
Re learn new hotkeys, that’s actually not been a huge issue. Most of them simply aren’t mapped by default, which is its own pain. I did a lot of bouncing between VSCode hotkey lists and the Obsidian hotkeys UI to align shortcuts. At least they do enable you to remap most every UI action. I haven’t used the built-in vim bindings, but supposedly they also work fairly well, fwiw.
For now, Obsidian + Obsidian Tasks just does way too good a job for my work journaling for me to completely ignore. Plugins do work around most of the more questionable behavior, though it does sometimes make for an inconsistent experience.