I've misspelled two names for trips with friends and only had a problem once, and that was with TSA. The first was misspelling Virginia with Vagina (I filled out Vagina the first time as a joke, then when I went back and legitimately bought the ticket I didn't notice that "auto forms" kicked in. Oops.)

Believe it or not, nobody batted an eye at that, but when I booked one for a Brian instead of Bryan, he went through the inquisition at MIA's checkpoint.

Go figure.