Hey Mathew I think meself and Kristoffer covered the bases well. Lots of ideas and experience there. Here in sunny twenty below (zero Fahrenheit) Manitoba in a town 3x population Kristoffer refers to gigs are pretty severely constrained. Try the Legion ~ an indoor busk. Check with management about protocols. Assisted living facilities a good bet because the private ones DO have entertainment budgets although you might need to adjust repertoire. In a lot of Canadian bars you can do the Mr Bojangles thing - drinks and tips eh. I was most heartened by your self-assessment of constant musical growth. You do not mention whether you are in small town or city. Kristoffer gave a good down-low on rural scene. Meself nailed the fee issue and lotsa + feedback. You have come to the right place! Very best of luck to you.
keep on pickin
dennis