@ledamarritz I never lived in Portland, but I'm from a nearby town and lots of my friends have ended up in Portland. My take: it's the biggest city in northern New England (ME, VT, NH) and as a result it has everything... very vibrant art scene, music scene, restaurant scene, etc. Like anywhere else in northern New England, get ready to deal with very long winters (but gorgeous summers/autumns!). You will need a car. Nightlife is fun except that after a while you will probably just be seeing the same people over and over again, which could be tiring or comforting depending on what you want. I think you have to want to be in a small city with a strong sense of community. Otherwise you will learn and experience everything there is in a couple years, and probably be left wanting more. But coastal Maine is great for families and anyone who wants to be able to be outside and have access to lots of outdoor activities (summer AND winter). Portland has an airport and once you jump on I-95 you're about 1.5/1.75hrs to Boston, 5-6hrs to NYC. Anyway Maine is great, go Maine!
"How to get away with being bad at your job" doesn't really go with "service edition", though. Because if you are bad at your job in a tipping system, you don't get paid. That's the agreement. These servers "got away with it" because they were lucky enough to have you guys at their table (case 1: understanding, case 2: tip a flat 20% regardless). You can't assume that they "got away with it" with other tables/patrons. They only thing they got away with was that they avoided confrontation over their service (we assume).