Heritage wise I've sold a few that I regret, but I truly feel blessed by all of the wonderful instruments that I've owned.
There was an early H357 that satisfied my Johnny Winter fascination that I sold. I think it went to a guy that I found out later owned several.
Heritage made me a remarkably gorgeous custom Sweet 16 with a 3 3/8" deep body, highly quilted back and sides, hrw pickup, and burnt amber back and sides with antique natural top. Oh yeah..it was X braced with routed neck pickup. It was something they did to make up for a terrible experience with the dealer Ed Roman. I loved it, but needed money for my guitar building/wood buying ventures. I tried to hunt it down through old eBay messages and emails, but the guy I sold it to had also sold it, and offered no information.
Then there was the most beautiful H555 ever. I bought it from Wolfe. It had intensely figured woods throughout with natural finish. One piece neck and hrw pickups. I couldn't get a bad sound from it. Again, sacrificed for the cause.
There are more, but the one I'd like to have back the most is a 1996 Golden Eagle I ordered new from bay state vintage guitars. It had upgraded woods with OSB finish, and an added tone knob. The neck was really cool. It was deeper than most, with a small heel and a soft D shape. I played the heck out of that guitar wearing the finish off of the back of the neck and a bit off of the pickguard. Again, a sacrifice for the cause. It was number 545.