I'd say plan your weekends to be in a good-sized city. Find out where the pedestrian action is for Friday, and where the market is for Saturday.   Be there pretty early on Friday, by mid-afternoon or before, and set yourself up at the most likely "pedestrian action" spot...work it until the evening ends.

Then if you can, force yourself to get up early just for Saturday mornings, and get to that market by 7:30 or so. By mid-morning, noon at the latest, you will have taken care of business, and are free to tour around or leave town, whatever strikes your fancy.

I once did $240 (noon Friday to noon Saturday) following this concept in Toronto. The pedestrian place was Yonge Street around the Eaton Centre, and the St. Lawrence Market on Saturday.

If it's the end of the day and you're in a jam for cash, there's not much to be had at supper hour (OK, my experience is the opposite of yours in this regard). Find out if there are any decent-sized concerts on in town and go busk the lineup. Fast $$.

Places: Montreal is fun, La Vieux Montreal (the Old City) is the place. Boston is OK. I found Charleston, S.C. a lot of fun (well, I was there on St Patty's Day).

In Vancouver, where I first busked, it always seemed that I was regarded as a variety of bum on the street. Can't get no respect. Granville Island Market is OK though, but crowded.

If you make it to San Francisco, my experience (mid-70's) was things are pretty loose, but that may have changed. There was lot of highly skilled competition and you really needed a theatrical style to make it.   

Have fun and keep us posted. What direction are you striking out in?

Bill
stayin right here