the biggest tip I can give you is not to act like the guy I met who tried a new tuning on his mandolin every day and was "influenced by indian trance music". It's probably advice you don't need though.

On a serious note though. Go for individuality. There's thousands of people out there playing guitars and singing. For people to choose you, you need to stand out from the crowd in some way. (That's why people who play the pipes or the harp or the dulcimer or something can make bucketloads of money sometimes-aside from being talented players of course which does matter too.)

Small towns are often better than cities but the money tends to dry up after a couple of days. Times people go out and are more or less generous can vary quite a lot from place to place, but a lot of it's common sense. Eg, spaniards and italians stay up later and even more so in summer etc.