How about Ireland or Scotland? For some reason I've been fancying these two countries lately, Anyone know how easy or not easy it is to hitch, busck, squat, or dumpster there? Locals friendly to traveler types?
Hitching in England (Great Britain + Scotland) isn't as easy as in the rest of the Europe, somehow people are afraid of hitchhikers and feel insecure, your best bet would be asking people for a ride in Petrol stations. Plus due to the fact that roads are inverted, you have to use your left and not right hand as usual, thats tiring atleast for me, don't know anything about Ireland.
Squatting in Scotland is quite a breeze, but there are many junkies and wreckheads who do nothing to help out to squatting community, just use ketamine all day long and drool. Dumpster Diving is also quite easy, but if you want to get something better from the dumpsters you need to get a bin key, cause all the good stuff is locked or behind a spiked fence. Friends had kind of a fights with other dumpster divers, you could say "turf wars", so early bird gets the worm... but you should be good..
Busking depends from city to city, for example in Aberdeen there are alot of immigrants from east europe, they won't give you a penny etc... but its a whole different story in Dublin where people are friendlier and warmer...
Because English is your mother tongue, locals should be more helpfull, because many people aren't very friendly to immigrants/travelers.
Haven't been to England for quite a while, so can't really help you out, just wrote my personal opinion...