I've gone 9 times including the last 6 years. Some tips:
Any prime strip sports book like Caesar's, MGM, Mandalay or Wynn is going to be insanely crowded. Getting there early won’t help as 75%+ of the seats will be reserved for comps and high rollers. It can work if you have a small group and are able to find a (standing) spot or corner but you’ll need to constantly be guarding your turf and getting drinks will be a pain (hint: tip the drink chick – a lot). I’ve heard that Caesar’s just remodeled their book and it’s about half the size it used to be. If so it will be even worse.
The free viewing parties get crowded as well. The original one was at the Hilton (I think it’s called something else now) and it’s huge. You might want to try it one day to get the feel – if you do get there early as it will fill up on Thurs & Fri. Treasure Island also has a free one. There are several off strip at places like Orleans and Palace Station which will be much less crowded. All are roughly the same experience – cheap draft beer and bar food for sale. I actually heard surprisingly good things about the one at Stratosphere last year, not sure if they are doing it this year.
I don’t think the viewing parties that cost money are worth it. I did the Cosmo one its first year in 2011 for $50 and it was OK, no way I’d pay $125 or whatever they are charging today. Ditto for the Harrah’s ones (Planet Hollywood, Flamingo, Quad). I’d rather have the $500 in my pocket to bet/spend as I see fit. In general you shouldn’t have to pay for most drinks if you are betting (more on that).
There are several bar/clubs that have deals, either admission or a minimum spend, like the Pub @ Monte Carlo, Emeril’s @ Palazzo, some bar in the Hard Rock which to me are similar to the pay parties. Plus they were mostly sold out 2 weeks ago. If you get in your likely going to be standing.
My group hangs out at the sportsbook in the Paris. We discovered it about 5 years ago. Relatively new and clean and in a good location in the hotel (right in front by the strip). There’s a bar in the sportsbook so your waitress isn’t trekking a quarter mile away for your drinks every time. We’ve met other groups there who we now see every year. The only problem is it’s gotten more crowded each year and they block off more seats/tables for comps or charge minimums. A group we know will have a table so we’re covered but as an overall Vegas event March Madness gets bigger and more expensive each year.
Some other spots to think about:
NYNY has a sports bar just up the stairs from their sports book (not really a sportsbook, more of just a wall with TV’s and betting windows where you have to stand) which used to be ESPN Zone. We used to hang at the bar in ESPN Zone and then walk down to bet when needed. It’s not a bad spot but also gets crowded.
We also used to spend time at the Flamingo sports book until they removed 2/3rd’s of it to put in a Mexican restaurant. Now it’s just a small corner of the casino.
The Mirage has a large book where you might be able to find a decent spot, there is also a bar right behind it.
The good news is that Saturday and Sunday are much mellower than Thurs/Fri and it’s much more likely you’ll be able to sit somewhere and watch all day.
As far as the drinks – make sure you are asking for drink tickets wherever you bet. It helps immensely to tip the bet taker. Give them $3-$5 every time you place or collect a bet and ask for a few tickets. We usually have so many unused tickets come Sunday we just start giving them away. Another good tip is to bet on horses as they make more money for the casino. They are more liberal with the tickets and you typically have dedicated lines with little to no wait.
If at all possible place your bets for the first round of games Wednesday night so you’re not worrying about it as you try to get settled Thursday morning. Even if you’re going to a viewing party which promises satellite betting do as much as you can in advance.
Keep in mind that pretty much every TV on the strip will have games on. That includes TV's at the tables, TV's in the lobbies, bathrooms, bars, walkways, pools etc. Even if you don't find a great spot it's really hard to not be able to watch the games.
