Royce,
Lot of info to unpack here and a lot of this is going to be personal preference, of course.
As far as your questions:
1) I wouldn't add a day of conditioning with your stats. You're young, not fat, and still have lots of training left to do.
2) You're LP is ending soon, so...not sure if there's a question here.
3) I think you probably would be best served gaining a few lbs a month from now until the end of the year, then you can cut.