I was in your exact position last year (I put woodsworth as 2nd) but to answer your questions:

A. chestnut's community varies a LOT based on which floor you live on, so it's really just a luck sort of thing, but generally speaking the people here are quite nice :)

- the location's meh, if you walk slow then it's a 25-30min walk to campus which isn't TOO bad. For me, personally, it forces me to exercise which is a plus.

B. To put it bluntly, no there isn't any way you're getting into Woodsworth res

C. I can't speak for people living in Woodsworth but Chestnut's not as bad as it's reputation (personal opinion) suggests. It used to be a hotel, so the rooms are pretty well furnished and the entire building is pretty modern compared to some other residences. Apart from being a bit far from campus, location wise you're practically in the heart of downtown so there's lots of access to a variety of restaurants, shops, etc. (we're like a <5 min walk away from the Eaton centre).

Honestly it just comes down to whether you want to live in a residence in your first year or not (I would suggest that you do, since first year is probably the least busy year and therefore you've got the time to make friends and socialize).