I have 3 tattoos. Two I love, one I don't. I have one on my shoulder, one down my ribcage and one on my wrist. The one I really dislike is on my wrist, the one that's hardest to cover up! I used to go to great lengths to keep it covered, but I just don't bother anymore. I don't really notice it. I've thought about getting it covered with a different tattoo, but it would need to be fairly big to cover it, and my wrist is skinny, so I'm not sure.
I guess the "will I regret it when I'm 60 thing" depends on why you think you might regret it.
If it's a design that you think means something to you now, but might not in the future = then maybe
If it's because you think older people shouldn't have tattoos = then probably, don't do it
If it's because you think your skin won't look as good at 60 = I don't think you'll actually care at that stage.
If you've had your heart set on a design for a long time, you'll probably love it. The one I have that I don't like was one I got on a whim.
Go to a really good, recommended place and ask them to draw it on you first. Then take your time really looking at it and make sure you love it.