I don't think you'll have to worry too much about what ppl think when you chop a long step, many ppkl think they look funny. (my self included)
And even if you to, who cares, it's your ride. I'm putting a caddy 425 in my Longhorn...and it is one of 1404 built. But that doesn't matter.
As for bed selectioon, you can use the box (- fenders) off of anything from a second series 55, up to an '87. The box stayed pretty much the same.
As for your inline, some one will want it, but it may sit on your shop floor for a couple years though.
Welcome to the club, from muggy Ohio.