First of all, know that many of the waitresses bringing you free drinks in Vegas get paid minimum wage. So people who tip the reccomended $1 a drink will get a lot of comped drinks, non-tippers won't.
Tip the $1 a drink. Although this is the reccomended amount to tip a waitress for free drinks in Las Vegas, 80%+ don't tip at all. Guess who the waitresses will keep coming back to?
If you're going to be there for a while (like a Sportsbook during a Monday Night Football game), consider tipping a $5. If you do, you won't have to tip again all night, and you can easily get 5-10 free drinks (which are mixed stronger for tippers) during the game.
If you're short on cash and with a friend, sit at some video poker games and very VERY slowly play on the minimum. Waitresses don't check to see how much you're playing, they just keep bringing drinks.
If you stay in one place, the waitresses will remember good tippers, so sticking in the same casino/area will help increase your free drinks in Vegas.