TW,
I used TiddlyDesktop for all that (except the 'classic' part) and it worked well when it didn't crash, which it did on a regular basis. The crashes were very random so difficult to debug, and I presume @Jermolene will be updating it after 5.1.23 (?) so maybe it will work better on OSX/Macos after that...
Both Bob and TD are easy to set up/use on the Mac. TD is actually easier to use from a UI perspective. But I'm liking Bob. :)