I've been to Vegas 9 or 10 times in the last five years, including solo, business, and with friends. For a short trip just to get away, I like solo. No worrying about who wants to do what, when, etc. I tend to do these trips as an overnight (maybe two tops) and power gamble (if you can call $5 tables power). Find the cheapest room available, only long enough to sleep and shower. I also have the ability (and desire) to travel more frequently than most of my friends, so it is much easier than trying to coordinate who can go when.
For group trips we have also had great times. Thankfully nobody in our groups is really big on having to stay together. The pool (usually Flamingo) is central base. Some are out there bright and early. I tend to drop by for a bit in the morning then hit the casinos once the sun gets hot. I usually go casino hop most of the day, maybe stop by the pool for a drink. Take a nap late afternoon. We usually just pick a time place to meet and head somewhere from there. If you don't feel like showing up, no big deal. When your tired, head back to the room. Never any pressure to stay with the group.
I'm off for another overnight (solo) trip next Friday. I saw $103 rate from DTW on Travelocity Dream Maps. Turned out the only way to get that was Wed to Wed, but got the 3:30ish direct outbound on Friday with the Saturday 10:50 red eye for $200. Free room at the Doubletree by the airport (unless something better opens for Hilton points). Look for me at the $2 craps tables at Casino Royal, or the $5 tables at Barbary Coast if I want to act like a high roller.