I live in Las Vegas. I don't spend too much time on The Strip... too many tourists
If you like Italian food, my favorite is Nora's Cuisine located on Flamingo between Decatur and Jones. They have a fantastic bar and a to die for wine selection. I highly recommend the Sangria. It's a little loud, so get a table on the dining side behind the sliding glass wall. There you can hear the music. They even have a Bocce court if you're into that game. Cap it off with Tiramisu and Cappuccino.
http://www.norascuisine.com
My favorite hotel is the Venetian. I like the art, and they have this amazing indoor area of shops, bars, and restaurants all around a river compete with gondolas you can ride if you want. The roof is painted like the sky, and it feels like dusk... the best time of day. Don't miss Fremont Street... it's old Las Vegas but so much going on there.
For shows I'm partial to The Beatles Love at the Mirage, or Raiding the Rock Vault at the Hard Rock. You should not have any trouble getting tickets. I hear Lady Gaga is coming for a two year residency at the MGM... that will be pricey. The Jersey Boys is gone... bummer.
If you're gonna gamble my advice would be to stick to table games you have the best chance to win. Black Jack, Craps, Pai Gow, and Baccarat have the least house edge, but I have only played 4 Card Keno the last several years on the machines. The odds suck, but a six spot will pay you a cool $400.00 on a quarter machine. Earlier this year I hit a seven, six, five, and four spot all at the same time, and cashed out $2,400.00
Best advice I can give you is have fun, and don't lose all your money on the first night. It would suck to be here for several days with no money. Good luck my friend.
There is the Mob Museum... I haven't been there myself yet, but I want to see it.
https://themobmuseum.org/