The High Roller is such a fun experience. Yes it's a little on the pricey side, but it's so worth it. I got our tickets on Groupon which was a great deal. Definitely check it before you get your tickets. We got two evening happy half hour tickets for $60 total. Normally, the evening happy half hour tickets are $47 so this was a great deal!
Personally, I think you should absolutely do the happy half hour ride and you should definitely do it in the evening. The High Roller takes half an hour to go all the way around and they have separate pods for the open bar (happy half hour) and the regular ones. With the open bar pods you get to drink all the drinks you could ever want, and it's not the cheap stuff either. It's top shelf booze and you can get mixed drinks, cocktails or even shots! You can definitely get your money's worth if you know how to do it. When we went, there were only two other people in our pod which was great! We could move around freely and had no trouble taking any pictures, and we absolutely didn't have to wait in line to get our drinks!
The view when you get near the top is amazing! You can see the entire strip and it's beautiful from every side. Be sure to take a few photos when you get to the top. As I said before, I definitely recommend going in the evening. The view is unbeatable and it looks so cool when the strip is all lit up! Definitely put this on your Vegas bucket list!