My limited experience in south east asia as far as accommodation is concerned is that unless it is a chain, there is very little difference between a $50 room and a $100 room. Normally I go for the $20 room because then my expectations are so low that I can't possibly be disappointed.
I guess you could have a good point there and it was frequently been a strategy that I used in the past. As I get older I find that I want more comforts in my accommodation but sometimes I start to feel that a more expensive place is simply going to mean that more people are at your beck and call as far as staff are concerned. Since I rarely even ask the staff to do anything for me other than give me the room key, I might be wasting my money.