I'm pretty set on keeping this particular truck for now until I build a dedicated cross country tow rig out of an obs I have. This one is already studded, deleted and has some other goodies, I've gone through pretty much everything mechanically on it, and it's optioned exactly how I want a truck to be, not to mention I paid cash for it 2.5 years ago.
An 8' bed truck would still take some ramp setup to work and tow a trailer, the sxs is about 114" overall length. I'm not too concerned about losing utility, I have several trailers of various style (car, dump, utility, gooseneck), if anything it will make the truck a little more useable for hauling pallets and such.
If you are dead set on using that truck to haul that sxs and pull that trailer, reconsider a frame swap or extension using factory pieces. IIRC, you have access to a shop, simply unstacking and restacking your truck on a longbed frame wouldn't be all that involved with a lift and a helper. Fwiw I paid 1800 for a rolling chassis 05+ 4wd. That may lead to a future title issue, which could be resolved by purchasing a factory new frame, sometimes they are surprisingly cheap, or just break it apart at the factory splice and weld in the rear half from literally any long bed super duty, 2wd 4wd 99-14?
Then resell short box for a pretty penny and install a long bed, or a 9' flat bed and roll out