I
can speak from experience with Callcentric.
Yes, call waiting with caller ID (and caller ID NAME, too) works as you describe. I have a 202 with 2 different Callcentric DIDs registered on SP2 and SP3, respectively, pointed to phone line jack #2 on the OBi. Call waiting works just as it should, even if inbound call #1 was made to SP2, and inbound call #2 was made to SP3.
Callcentric supports (by default, if you configure it on your OBi via the OBiTALK portal's canned settings for Callcentric) both MWI (the stutter tone) and VMWI (the blinking light) feature for new voicemail messages. The VMWI indicator will promptly turn off after you listen to the messages.
If your attached analog telephone supports those features, then they will simply work.