I know a couple of guys who did this for various times.
One was a mentor of mine. Another was a guy I rolled with briefly before he tried to finagle his way into using my already-crowded apartment as a storage space.
The mentor of mine used to tell me, "If you want to get really good with girls in a serious hurry, try not having a place to go back to at the end of the night. Then you either find a girl who'll let you sleep in her bed no matter what, or you sleep on the streets. Sometimes you might have sex with the girl, sometimes not, but the goal becomes a hot shower and a warm bed even more than the sex. After a couple of nights sleeping on the streets, your motivation to pick up just so you don't have to sleep on the sidewalk anymore will be through the roof."
At one point, long after he had plenty of money and didn't need to do this anymore, he went and crashed in a city for a couple of weeks without a place to stay because he felt like he was getting soft and wanted to get some of his old motivation back. Within a few days he was shagging girls behind vending machines and in half-finished construction sites. Ended up staying with a really cute girl for a while at the end of the trip, before it was time for him to fly back out again.
Chase
