The answer to Q1 and Q2 are likely both "YES". The strategy I would suggest you to take, since you have a latitude ticket, is to continue monitor the T+ price. If you don't get a confirmed upgrade by T-7, cancel your latitude reservation and get a full refund, then immediately buy a new ticket at T+. (actually AC IT is a bit sloppy lately and you can do a duplicate booking into T+ before canceling your latitude).

Some anecdotal evidences suggest that the upgrade waitlist is reviewed right at T-7, and then again at T-2, even with R remains at 0.