Welcome to the Highlander Radio forum.
Living in the Boston area myself, I can vouch that there are many opportunities in the night clubs for entertainers. I am no expert on this matter, my interest are purely in Celtic music and such.
There are a number of advantages to the Boston area, we have a lot of irish/scottish decendents that might be interested and accept your entertainment. There are lots of college kids that need entertainment at the clubs! (& drinks too). Boston is located in New England, very accessible to 7 - 8 states all within an hours drive.
The cons: It is very expensive to live here! Traffic is terrible and in Boston there is the world's largest public works project called "THE BIG DIG". The say that Rome was not built in a day, but that same anology can not be used fo this project. A constant state of construction in the downtown.
That's pretty much all the advise I have to offer. Perhaps someone else can kick in a few ideas.