I'm not the original poster, but I'll take a stab at this. I've been checked in to as many as FIVE places in one weekend -- used the same credit card without a problem. I drive into Vegas, so getting from place to place is no problem. Free play amounts varied greatly -- probably from $200 to $1000. Golden Nugget was $700 most times and it was not broken up into three days. The only hotel to ever check me out prematurely was the Rio, but it didn't matter as I had already given them my play and used my offer.
I still double book on occasion. In October I was booked at Silverton for a golf tournament and $400 free play. I gave them $49k coin in and lost $275. I was also booked at the Mirage on an offer with a suite, RFL, and $700 free play. I gave them $61k coin in and won $7200.
Going back and forth does get to be a hassle, but sometimes it's just too worth it not to do it. However, I am into a bit more mellow trips now and will only double book if I'm taking an offer from somewhere I don't want to stay. I'm booked in April at The Hotel with only $150 free play just because I really want to stay there again. I've double booked at Four Queens because I like playing in the casino there and love enjoying a nice meal at Hugo's, but I don't want to stay in one of their rooms. I'll happily take my $200 free play as well.
I'll also double book if I have a family member or employee that wants a room.
There you have it.
Edited to add: I leave for Vegas tomorrow, staying at Bellagio on an offer of a slot tournament with food in limited restaurants. I haven't double booked anything because I really just want to relax and enjoy the Bellagio experience.