I defer to Matt's superior experience in this realm, but I'll say that even a relatively new sailor like myself really has no problem single-handing my H16, although I'm reluctant to go out in heavy air solo just because I don't have the weight to right it myself if I were to go over. A righting bag would probably help here, I just haven't been able to prioritize that expense yet.
You can get used H16s at pretty good prices, so I'll go ahead and recommend you at least look at this option. I've sailed with three adults (myself included) on my boat several times now and it's kind of a dog with 425lbs but still far faster than a Sunfish or something. LOL
Good luck broly!
"A little crazy but with big balls."