October move in: logistical nightmare (Boston: sublet, apartment, to rent)

[e-rock]

I have a logistical problem that needs solving.

I will be subletting June and July in Boston (studying for the bar). I will be out of the country all of August and September (post-bar trip!). I start work in Boston in October and would like to rent an apartment with an October start date somewhere in Beacon Hill or South End ($1500-$2000 range). Craigslist has countless listings for places starting in September, but hardly anything for October. It seems like everything in Boston revolve around the college schedule, but I don't plan on living in a student-heavy area.

My questions:

1. Am I going to have a difficult time finding something with an October start date? Or am I just too on the ball and starting too early?
2. With these places with an October start date, when will the bulk of them become available? (I don't know if there's a 30 or 60 day notice law in Boston.) Then only time I can look at places is June/July.
2. Should I just get something with a September start date and sublet it out that first month? Advantage: lots of places to choose from, and I'll definitely get the place I want. Disadvantage: I have no idea how I would implement this--from inspecting the place on move in, to finding a subletter that needs an unfurnished place for 1 month--while I'm abroad, and I definitely don't want to blow away $1500-$2000 on rent.

Thanks for your help y'all!

[xS☺B☺s]

It would seem to me you could sublet again in October to search for a permanent place.