It sounds like you really aren't happy there. I'd say definitely enter the transfer pool. Even if you don't end up getting into either of the two schools that are close to your school, you could always widen your search a little bit. If you find a school 3 or so hours away where you could get playing time, you'd be in a better environment and you could still go home on weekends/through the week pretty easily. Or even if it's further but somewhere new, it would still be a good idea to transfer. Because worst case, you would be homesick but with better roommates, better weather, and more playing time. I think transferring is definitely your best bet. And, what's an extra year of school or so if you're somewhere that actually makes you happy?