Yes, you'll have trouble getting a cab back unless you have a cab drop you off a few blocks away from the strip -- like maybe Ellis Island -- and you walk the rest of the way but I think by 10 it'll be crazy.
Last NYE I stayed at Caesars and went to the Stevie Wonder concert at Cosmo. I wanted to eat at Milos and didn't have a reservation but there was a space at the bar and you could order appetizers or an entree at the bar. I ordered a drink and a sample of appetizers and the bill was about $150, including tip. I was dining alone and had a great time because folks on both sides of me at the bar were conversant as was the bar tender. If you are dining alone, Í'd try the Cosmo bar, maybe even if you are with someone, or grab a meal elsewhere on the strip if not at Cosmo. If not dining at Cosmo but on the strip, I'd make it an earlier dinner so you are not fighting the crowds as much getting back to your hotel.
