I went through this process. Rode a Huffy for years. I gave it to a friend when I moved. Bought a used bike, then a Wal-mart special. Neither lasted more than 3 months. I couldn't take the Wal-mart bike back after it broke cause I lost the receipt.
I went to a small bike shop and after some reluctance I bought a Trek 820. Got to be the best $275 I ever spent. After a year I'm still tickled with it.
Now I want one of the Trek hybrids but I can't get my cheap ass up off of $750 for a bicycle.
I am in the market for a second bike. I saw a Schwinn for $300 that I liked.