Good experience for both trips I had last year (both Back Bay to Logan only).

I am NYC-based. Sometimes take advantage of cheaper fares ex-BOS. Buy $3 tix ahead (as mentioned, tix is only collected to airport; from airport is free).

As far as traffic is concerned, it should be a consideration, but if you leave enough time, should not be an issue. I have made both trips well short of 30 minutes from Back Bay.