For us, it wasn't a good fit because of what we'd already done/been doing. As for the people we've met who've said they had a less than fulfilling experience, they didn't strike me as having any psych problems. To boil all the feedback down from what we've heard - again, I think it comes down to expectations that weren't met. Examples: the places the Ha-Ha stops (Santa Maria & Cabo San Lucas) didn't have the "feel" of being in Mexico for some people & they realized too late that they'd wanted a bit more of that; on the other end of the spectrum were folks who I gathered might have expected more assistance or support from other boats than was appropriate to ask for.
Going on the Ha-Ha is not a life-fulfilling experience for everybody. Nor is something wrong with someone who regrets having done it. People have the same things to say about having kids.