Yeah its just you then
1st lifestyle changes, get something that means something to you when you get it. I look at tattoos as sign-posts for where I've been in my life and what's been important to me, that way no matter what I get I have no regrets as it meant something to me at that point in my life.
2nd, my wife has tattoos more than 20 years old and they look just fine. Go to a good reputable artist who uses quality ink and don't go drunk or stoned.
3rd, I wear a shirt and tie to work and have full sleeves. Whenever I'm not at work I go with short sleeves all the time but in the business professional world there's aboslutely no reason that you can't have tattoos.
So I definitely respect your reasoning for you regretting your tats but I will respectfully disagree with all of your points. I don't believe tattoos look stupid at all. I think that if you get quality tattoos it will look just that... high quality.
Get tattoos that are high quality by a professional artist, don't go stoned or drunk, make a logical informed decision and have it be something with meaning and you'll never regret your tattoos.