I've used Michael's Moving a few times. They've always been super helpful and priced fairly.

If all theee of you are part of an active lease, then everyone is still liable for the rent. Even if they no longer physically live there.

It should be up to them to find suitable subletters to fill their spots in the lease and remove their liability.

Not so much. The housing market is more geared toward spring and summer,, but there's always something for sale.

In my opinion sellers who don't sell and have a house sitting on the market around the holidays get a little more desperate to sell.

Yes, greater Boston and Massachusetts generally follow a September move in schedule.

Luxury new construction apartment buildings will have leases expiring year round, but most small mom and pop operations will be September 1st move in.

Not roof access, but if your looking for the best views of downtown Boston, the Reel House in East Boston has the best views in my opinion. There's a public park there you could sit at all day.