Yeah, I just finished writing mine and was thinking the same thing. The bad points for me were 1) I completely decimated my savings, 2) I had no health insurance and didn't realise why this was a bad thing, 3) I got frustrated at times with the fact that "van-dweller with no fixed address" is not apparently a draw card with the ladies.

Fortunately "inability to connect with people" wasn't an issue for me. But I stayed out of the big cities for the most part, and a clean-shaven face and mischievous smile can go a long way in getting conversation started.