@Ben_Boyle,
For some reason, I’m not running into your #2 and #3 issues (current Chrome on Mac).
FWIW, I wrote this post a long time ago about inserting tables in Asana task descriptions which, if it still works, should work in Comments too:
You can create real tables in Asana but only in the Overview Project Brief currently.
Hope that might be of some help,
Larry