I'm wondering if taking some planned maintenance breaks during my weightloss will help the skin keep up to the losses.

right now this is all theory of course, but I'm wondering if I diet and exercise till summer, then maintain and continue exercise over the summer my tummy will fare better in the long run. Or should I just not tempt fate with even a planned break and keep on it.

mind you, me even making it on a diet till summer is a bit in the realm of science fiction given my past diet history

Unfortunately, choosing the right parents is the best determinant of whether you will have loose skin.

Yeah, the amount of saggy skin in the long run would remain the same. Saggy skin can be more noticeable for those that lose weight very quickly just because skin hasn't had a chance to catch up but it doesn't effect overall amount of loose skin.

Well, I've been maintaining for the last year and a half and my lose skin is about the same. It could be my age though. I wouldn't worry about that now. Just focus on your weight/health goals. Add some strength training exercises. If in the end you find that you absolutely can't stand all the lose skin, there is always the surgical option as well.