Saw the other discussion. There was some bad information there. I also figured it might get more attention to have another thread.
The big difference between a Boston nightly rental and what we do on the Cape/Islands and Berkshires is when the reservations are made. Most of the seasonal reservations are going to be booked before the end of March...where the nightly stuff happens much closer to the actual stay.
If Airbnb doesn't do something to service the weekly vacation host quickly we'll all just move back to the way it was done before. VRBO, Local realtors, etc. Airbnb made the s/t rentals that are happening in Boston possible, but the ones on the Cape/Islands/Berkshires have been going on for decades. The State also needs to have Airbnb involved if they hope to really be able to collect these taxes. Otherwise, it'll just end up like the self-reporting of Use Taxes (you know like when you don't pay sales tax on something in New Hampshire and bring it back to Massachusetts).