John,

I wouldn’t worry too much about about being in the same place as I would thinking about how often you want to perform and how many songs you have in your repetoire.

It also depends on your personal reasons for performing. If it’s mainly for fun, then one night a week may do the trick and would obviously put less pressure on you.

If it’s also about the money, then mo’ gigs = mo’ money.

If it would be more fun for you to play in different spots through the week, then I’d be hesitant to accept more nights from your current employer. If you accept Wed and Thur from him and later find someplace else you’d like to play on those nights, it may be hard to make that change without ticking him off.

If your current employer would allow you to leave most of your equipment there for a 3 day gig and it would be safe, that would obviously be a big plus.

These are questions only you can answer. Just giving you some food for thought.