I don't have any tats myself, but as a younger bloke several of my mates have prominent tattoos.
One chick I know has a huge phoenix on her back, and I mean huge. It looks very good, and it has a lot of meaning to her. Because it's on her back, she can hide it easily when working ect.
Another bloke has some all over his arms, military themed, also with the names of his kids on his forearms. Again, it means a lot to him and he can cover them with long sleeves if he needs to look professional.
I understand tattoos like these, and reckon that they look really good. They also have personal meaning, and with that in mind it seems less likely that they will end up regreting them.
What I don't get is tats that are just pointless, currently fasionable trends, such as tribal tattoos, kanji characters that you cant even read, random butterflies and flowers. I reckon those are the kind of things that people will regret when they go out of fashion - just like the chinese dragon style ones that were popular a couple of decades ago...
All that said, I had a good chat about it once with the chick with the phoenix tatt, and her response was something very much along the lines of the following pic.
Maybe she's onto something lol