Help me choose... (Please)

Your Southwest non-stop flights to LAS are really nice...7:25am depart-8:55am arrival Sun- you can leave your bags with the resort you choose and in the past they have allowed us access to pools to hang out at until our room was ready. It's a nice quiet time to arrive,
Leaving Vegas at 1:45 and arriving home at 8:55 is also nice...no early morning rush to the airport.
I would consider these.
I would also like you to consider a Sunday-Friday stay. You had mentioned budget, a Friday night is usually jacked up. Also, arriving so early Sunday would give you really an extra day. You would have to take a 11:55 nonstop flight unless you don't mind stops. Also, do the Southwest Vacations to price flight & hotels. It looks like you could do a Sunday-Friday stay with flight at some decent resorts (Monte Carlo, Mirage, NYNY, Flamingo, etc) for under $1,500 for 2. Don't forget many resorts tack on resort fees...don't get bummed out about it, just figure it into your per night stay-not much you can do about them. We have been able to get great deals out of Milwaukee.
I would also like to pass on advise I give to friends who are newbies, don't burn out by trying to see IT ALL. That's why I feel a Sun-Fri stay is always nice. We don't want you burning out and saying "not going back". Take your time, enjoy it, and look forward to planning and going back time and time again like most of us on the board. Heck, we have 8 trips and I consider ourselves newbies. But we learned so much from others here.
Hope it works out and we're all here to answer questions.

 

For your budget, I would spend just a little more $$ and stay at Flamingo or Mirage. Both have awesome pools and great location on the Strip. 1st trip you really need to be in all of the action IMO

 

Ditto Ditto Ditto on the trying to see and do all. I ruin our first trip trying to do exactly that.

Out last two trips, we have done the arrive Sunday, fly out Friday afternoon trips and really enjoy them. Saves money on the big Friday night hotel jack up prices, and Friday is crazy busy. If you want crazy + over the top crazy Vegas, include Friday and Saturdays. If you want a more peaceful, Do the five night Sunday - Friday. The strip is still crazy fun on the weekdays.

Last, we love the 5 night Sunday - Friday trips. For one factor is cost, the second is cost, and finally the third is cost. The meals, gambling, other expenses add up.

Plus, when you do Vegas a second time, you have a better idea of what you want to do the next time. Enjoy!