I dated a woman far, far wealthier (I drove a 1995 wrangler, she drove a brand new 745) than me for a while (I say with a little weird, misguided pride that the next guy she dumped has appeared in a MLB Allstar Game). I certainly didn't mind the unsolicited gifts, trips to her family's villa in Spain - I would've married her if things worked out. She was surprisingly grateful for what she had and really really nice. Alas, things did not pan out. I've dated a few other wealthy chicks (all but one of whose wealth is from their parents)
It does introduce a weird dynamic - they really don't need a guy to provide, yet are still programmed to seek out a provider. So, in my experience, as long as you try to be ambitious and make money, you'll do alright. The con - you'll never make as much money as Daddy did for her, and your gifts have to be extra creative - you can't just throw money at her.
Sorry for the slightly misogynistic tone.