Is 37' to much for a shortbed SRW??

I don't get into weight wars, but I will comment on your trailer and truck. I have basically the same rig, except a 2002, and a similar RV. The one piece advice I can give is buy a slider. Yeah, it's not always necessary, but it sure makes hitching and unhitching for me much easier. With my old hitch, I could not let down my tailgate. It was a real pain making sure I backed up far enough to raise the tailgate, but not so far back my tailgate hit the fifth wheel. Now, I always slide my new hitch in the maneuvering position so I can raise and lower my tailgate and easily hook up the lights. I slightly bent my tailgate once pulling forward a little to far, so the extra investment is worth it.

Found my slider on Craigslist for $200, so look around.