On Question 1, it'll blow a hole in a budget that's already strapped. I don't buy booze that often and when I do I usually get it at BJ's where the prices are already discounted bigtime and the excise tax isn't that big a hit.
On Question 2, I think 40B is essential, particularly where you have schools largely funded at the local level by property taxes. The rich kids go to the rich schools in the rich towns and the poor kids go to the poor schools in the poor towns. That's a bad system. 40B helps a little bit.
On Question 3, I'm surprised that you support it. Even Charlie Baker realizes it will be a disaster if it passes.