60 $1 bills should be plenty. You don't have to tip for each and every drink. If you are planning on staying at the same bar for the night you can tip when you leave for the night. If you are staying at the same hotel it is proper to tip housekeeping on your last day. Tips with meals can be added to your credit card or paid in cash.
Upstate, don't give him that crappy advice !
You tip right from the beginning !
You'll be served promptly each and every time afterwards.
The best advice is to tip good , and you'll never need to wait in line ever again.
Everywhere I have been it worked really well.
I'll never forget those times that the bar had a 25-30 people line-up and all I needed to do is sit down, and was served within seconds !
Sometimes I would just tip $5 or $10 in advance if I was planning to stay there for a longer time being.
I met another fellow Canuck, I think he gave them a $100 in advance and just told them, please take care of me for the rest of the week.
He was served just like myself - never had to wait in line and served promptly !
A few extra bucks goes a long way (you'll notice it yourself, that others that don't tip, can wait forever, be it at poolside or the inside/outside bars).
(Those are usually the ones that then complain about bad service on reviews ) !
As for room service, don it as well, - leave a few dollars every morning for house cleaning. It also goes a long way.
You'll be taking care of everything, including the bar fridge filled up good (if you have one), but also get better cleaning, new shampoos, and even the bed sheets changed almost every day.