Sleeping rough is towns is quite possible, if you sleep in front of a shop in the center of London, nobody really cares. Also, many apartment blocks have stairs that go past the last floor to service areas (for lifts etc) These are usually locked, but you can sleep in front of the door.

It's mainly a matter of confidence, I've slept on Raststaettes, inside, in the closed part of the restaurant, outside, just finding a quiet spot, under motorway bridges (usually pretty dusty, but always dry), on building sites and even out and about for everyone to see on benches and walls.

Robert
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Robert AH Prins (254,000+ km and counting)
robertdotahdotprins on the big account from Google