Love Vegas!!
Go every year with the boys....you'll have a great time!
The Quad is the re-named Imperial Palace - it's a shit hole, avoid it!! The rooms are disgusting, and given the 4* & 5* hotels available at relatively cheap rates you can certainly do better. Also avoid Circus Circus & Riveria for the same reasons. Luxor is usually cheap, as is Flamingo & Harrahs although none would be my pick.
If you can get a decent price, any of these would be ideal - The Cosmopolitan, Bellagio, Mandalay Bay, MGM, Planet Hollywood, Mirage, Caesars Palace, Wynn, Encore, Treasure Island, Venetian or Palazzo. Depending on when you're going you'll want a decent pool - Mandalay Bay, MGM & Encore have great pools.
If it's your 1st time in Vegas, then you want to stay on the strip - all of the above are on the strip.
Yes, you get free drinks when gambling (including champagne at The Wynn) and if you tip the cocktail waitress well she'll be your best buddy & keep the drinks flowing all night.
All of the top hotels have great clubs (XS at Wynn is my favourite) and fantastic restaurants. Although the hotel is terrible, my favourite place to eat in Vegas is The Steakhouse @ Circus Circus - it's cheaper than other steak houses but regularly wins best steakhouse in Vegas (and that is some feat)! Make sure you go over to Voodoo Lounge @ Rio - it's a club on the roof & the views of the strip are amazing (as are the views from The Foundation Room at the top of Mandalay Bay). If you go to The Stratosphere (and I would), don't pay to go to the observation tower and instead go to Lounge 107 (it's free to get in & is only one level down from the observation deck - which you can go to after the lounge for free if you want) for Happy Hour drinks!
As for shows, Absyinthe @ Caesars is supposed to be hilarious but I genuinely loved Matt Goss, who sings @ Caesars. Fell asleep during Penn & Teller, but that may have the drinks before hand. Love @ Mirage is also fantastic.
If you're doing the Grand Canyon then I recommend Papillion, who do various helicopter trips. We did the early morning one & was back at the hotel for lunch!
Taxis are fairly cheap, but you may find pre-booking a limo for the 10 of you a cheaper option from the Airport. We use Presidential Limousines and they are very good and inexpensive. You book an hour, so you can stop off at the Las Vegas sign for photo's & grab some drinks on the way.
If you're going lap dancing (and there are 10 lads, so i'm going to assume that you are) then Treasures is our preferred club - you'll see why when you get there.
That's probably enough to be going on with, but if you have any questions i'm happy to help. I love Vegas!!!