Hollywood tickets are considered part of a group of 25+ that can arrive at a later time (Arrive at 12 noon for the 4PM taping) even if they don't have enough people. You will not be able to go as part of the hollywood tickets group if you attend the first taping - because to attend the 2nd taping as part of the hollywood tickets group you must be physically in the line for the 4pm taping at 12 noon. However, if there's room left in the 2nd taping after the 1st taping has finished, you can get back in line after the 1st show has finished and see the 2nd show. You won't even need any sort of tickets - they'll just give you new contestant cards. From what I'm hearing they are looking for paid audience members for this week (I will be attending May 12 and 13), so I'd say your chances are good for getting to see both tapings.
Attending multiple tapings does not affect your chances of being a contestant - but Stan does change what questions he asks people if he knows you were at the earlier taping. Good luck to you!