I'm a Junior, and that has caused havoc with last name misspellings for as long as I can remember, especially since computers became popular. At my current employer, the Rather Large Airline, they originally entered my last name into the HR system as MANNJR (even though they do have an option for surnames!) It took complaints to the HR people multiple times to finally get the issue resolved, and there is still one system that shows my name as MANNJR there.
Any time I list for a flight on the Rather Large Airline, it pulls me up as CHARLES MANNJR in the reservations system. I have tried to get this corrected but the people I have spoken to about it told me that they have to leave it like that to distinguish between me and my father. I've tried explaining that he is deceased, and thus not likely to do much non-revenue flying, but it's been to no avail so far. Sometimes correcting this problem is like banging your head against a wall.
My favorite experience with the surname was when some phone solicitor reading from a script kept referring to me as "Mr. Mann Jr." on the phone. I hung up pretty quickly but it was kind of amusing. And of course, since my full name is Charles Mann, Jr. it allows me to make lots of "Charles Manson" jokes. (Well, to some people that's disturbing but I always get a kick out of it.)
While I appear to be a confirmed bachelor for now (although I never say never) if I do ever have a son of my own I can guarantee I will not continue the naming tradition, even though that's popular here in the South. Plus, I think having a full name of Charles Shelton Mann, III, would just sound too lawyer-ish. I suppose Trey would be a cool nickname, but I'd rather that whatever offspring I have has a name of their own.