After being to Vegas over 12 times I personally have a tradition every time I go (all statements are in my opinion):
Places to Eat/Drink/Things to See
-If with a group who drinks go to the Fuel Bar in front of Bally's, next to Sin City Brewing.
-Yardbird (in the hallway between the Venetian and Palazzo next to La Chica) for their weekend brunch -best non-high end meal om Vegas
-If you like wheat beers the Walgreens directly across from Crystals City Center Mall is the only one on the strip that carries Franziskaner
-Chicken Sandwich and Ramen at Momofuku (Cosmopolitan second level) for one dinner
-If you are in town during the SEMA show in November they park a number of the kitted out cars in front of the Aria, worth checking out.
-The Grand Lux Cafe at Venetian and Palazzo are the best all night food in Vegas, very consistent quality, even at 3 in the morning.
Places to Play
-Best for table games - The Cromwell has the best (aka most engaging) dealers on the strip. -Almost- everywhere on the strip (as of November 2019) were 10$ at all times with some doing $15 min bets at peak hours. You can still find $5 at Casino Royale and TI on off hours, but otherwise you'd have to go downtown for "cheap" games.
-Best for Poker - I have less experience with live poker in Vegas, but I do know Venetian has the worst tournament rake in the City (though they have the nicest room). If you're looking for experience playing at the Bellagio next to Bobby's room is pretty cool, even if it's just 1-2 cash.
The best value for money in hotels:
-Low tier - Bally's: Central location, clean rooms with everything working (which is a surprisingly tough bar to clear for some places like Luxor)
-Mid tier - Ceasar's Palace: Good(ish) comp program if you play and stay there, good location.
-Upper tier - Cosmo or Venetian/Palazzo: best restaurants and pool areas, Cosmo's hotel reward program also carries over to other Marriott properties (I believe, check the website). Venetian/Palazzo are all-suite, so even the standard rooms have a sunken living space with plenty of space for entertaining or hanging out during breaks.
-Boutique: I have personally never stayed at the boutique hotels (Nobu/Waldorf/etc...), but would be interested to hear what they're like.