When I'm on the road I only stay at people's houses if they enthusiastically invite me.
I then have a rule not to stay at somebody's house for more than 3 days unless they enthusiastically invite me longer. My dad used to say, "After three days a fish stinks."
If you aren't comfortable camping and can't find a place to camp anywhere you go, whether in the city or the country, I wouldn't recommend you being a vagabond.
Yes, I house-sit. But, again, it's the same principle. I never ask to house sit, nor do I advertise that I house sit, nor do I look for house sits. People have to actively seek me out and ask me to house sit. Despite this, I actually get quite a few house-sitting requests. Sometimes they last a week or two, sometimes a month or a whole season, sometimes consecutive house-sits one after another. House-sitting usually involves taking care of animals. It's a nice convenience sometimes, but I can take it or leave it and am usually very happy to return to camping out, where I feel freer and healthier.