The Ha-Ha is a real mixed bag. You're correct that several Ha-Ha alumni use it as a way to determine whether they & the boat wish to go further & make an ocean passage. Others just like the 2 stops the Ha-Ha makes & aren't interested in exploring Mexico any further. We know this one guy, who's done it 7 times. Lots of repeat customers in the Ha-Ha. The parties, I hear, are pretty fun. And you get the T-shirt & the burgee. But we didn't want to spend - what is it now, $350? - for stopping at only 2 places when we were coming down to Mexico anyway & wanted to explore the Pacific side of Baja, knowing we'd likely never pass that way again. For us, *not* doing the Ha-Ha was the right choice.
My point is - and this partially answers Paul's remark below - that there are many Ha-Ha'ers & other cruisers who say they have years - even decades - of experience, but have never sailed overnight, never stood watches, never had to do much more than eyeball navigation; nor sailed a leg longer than 70 miles, nor even anchored. We've met them. We've also spoken to several Ha-Ha alumni who were less than positive about their Ha-Ha experience - generally sounded to me like expectations (realistic or otherwise) that weren't met. Interestingly, they were all first-timers.
Didn't say anything about sailing in the "right places." My discussion is about what various people mean when they say they have "experience."