I don't spend a bunch every month, but I do spend more than I need to. I don't "deal" shop. I usually go out on a weekend looking for a specific game with a set amount of cash in hand. If the places I stop have it, I'll get it. If not, I usually grab a few smaller items worth the same amount and try again next week elsewhere.
I always buy from resellers. In this day and age it takes a lot of courage to have a private business selling games. I like to endorse that, even if it costs me a bit more. Buying online, unless it is something I haven't had any luck finding otherwise is usually my last resort.
If I had significantly more money to spend on games I think my attitude towards my collecting would change. I don't want to say I feel ashamed, but I am definitely reserved/conservative. With more cash I think I would be more confident in collecting and really going after what I want. I don't see my self buying more, but being willing to spend a little more to get the games I really want.