I booked us a hotel on Ko Phangan that looked rather nice in the pictures. It only ran us about $22 a night and we're splitting it by two so around $11 a night each (not too bad!). Plus its only 5.6 miles from Haad Rin.

Im not necessarily looking for full blown luxurious comfort, but I don't want sketchy hole in the wall either. I think I would be able to swing $50-60 a for sure which you say will bring some more comfort.

I read that a bucket of liquor will run about 200THB so about $5-6 USD. Not too shabby for a pint of liquor haha.