Some recent recommendations, since I was there with the wife for my 40th in September and then with a group for a wedding in November
The September trip, we hit a lot of the regular spots that we mostly heard about in this thread (Frankie's, Peppermill, Yardbird, & Mon Ami have become the big 4 must-hits every time we go now). Also made it over to Hugo's Cellar. The ribeye was awesome from what I remember, but we were really banged up from pre-dinner cocktails at Frankie's. Three "5 skull" drinks and a Kahiki Kai for me was a biiiiit much after day drinking by the pool all afternoon. Other new dining spots were Rose.Rabbit.Lie. at Cosmo and Mott 32 at Venetian. I expected Rose to be more, I dunno, snooty or something. Not sure why, maybe because of the way they write it out. But after some drinks at the nextdoor speakeasy, we got inside the restaurant to find a guy tap dancing on top of a piano and a large woman in a bushy blonde wig singing show tunes. Fun night. Mott 32 was just incredible. You'll spend all your winnings there, but it's worth it. We let the waiter recommend a number of small plates, and each one was better than the one before it. Easily one of our best Vegas dining experiences overall, and really unique drinks too.
First two nights at Cosmo, most of the days spent day drinking at the Boulevard pool. Very laid back, awesome views. We moved over to Venetian for the last two nights, and I don't love what they've done with the pool over there. They've added a lot more seats, but they chopped the pool up into like three sections to accommodate the additional seating. Anyway we went over to the Palazzo pool where there was more room. Side note - we actually stayed at the Linq the first night we got in. We're from NJ, so to beat the jetlag we fly out at nigh and stay up as late as we can the first night. Wake up the next morning at normal Vegas time and boom, good to go. But since we're only gonna use the hotel to sleep that first night, we just go with whoever offers a cheap deal. Got a nice discount at the Linq and I'll tell you, the room was pretty good for the price. Had our own private little patio with some couches that led directly out to the pool through a gate. Had brunch at Hash House. Big portions, but the food quality and atosphere weren't on the level of Mon Ami.
Far as night time options, don't ever go to Little Darlings. It was horrific. Salvaged the night elsewhere thank goodness.
Tried out some new bars (Downtown Cocktail Room on Fremont, and The Dorsey and Rosina at Venetian). Stuck with the Chandelier when we were at Cosmo, where my drunk wife asked an equally drunken bachelorette party if any of them wanted to come back to our room to help us celebrate my 40th. God I love that woman...