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Honestly, June 1 is probably going to be your best bet in regards to locking in a good deal. You will also avoid all of the chaos that is right around September 1 for moving in.
Pro
Not August 31/September 1.
It’s been awhile, but my wife and I rented in the South End on an off-cycle (not September 1) lease and moving in the middle of July was easy.
Do not,
DO NOT move on 9/1!
Thank you!! Noted. What’s so bad about Sep 1 and why do so many people move then?
The vast majority of leases in Boston are 9/1-8/31 which makes it difficult to find places, when you do they are more expensive and moving is generally not a great time with everyone moving into apartments and college kids moving into school at the same time
The corporate/institutional housing companies manage most rentals. They want everyone's lease to end at the same time, giving them the opportunity to jack up rents during renewals since everyone is looking at the same time.
I saved nearly $400/mo on my apartment when I signed it on 9/15. Anything unsold on 9/1 gets discounted.
Additionally, you'll have a hard time finding moving trucks, traffic will be bad, and there'll always be someone who stuck a truck under a bridge on Storrow.
If you sign an off cycle lease, you'll typically see discounts/offers on a non traditional 12 mo lease to adjust it to end on 8/31.
Do not fall for it!
I used to locate roommates through Bostonapartments.com. They still offer this feature. https://www.bostonapartments.com/