The most I have ever spent was on a small Fendi that I think came out to $480. I have a Louie V bag that I think is in the $500-$600 range, but an ex paid for it lol.
Right now $250-$350 is around my normal price for what is comfortable on my salary and life style. The last few bags I bought at Coach have been in the $300s. The $300-ish bags give me the freedom to have a couple a year, which is more fun. I love to shop. Maybe if one day I had a lot more money, I could see spending up to $1,000. But even if I were rich, you'd never see me with a $5,000+ bag...I think it's just a waste to have a bag that expensive. I think there needs to be a limit for me.