I pull with a dedicated 1994 F350 CC DRW, 460, 4.10. It's been a garage kept, dedicated tow vehicle since day one. Right now it sits at approx. 50k miles. 100% stock with the exception of a full Banks, K&N and CD player. 100% original except brakes/tires. Every year I look at new deisels, but just can't justify it. Mine is paid for, tows like a champ, and I know the truck. As others have said, older is easier to self-maintain. Sure I like the bells/whistles, power of a deisel, etc. on the new trucks, but I can buy a lot of stuff for the $60,000 it costs to replace mine with a new deisel. Plus, it's now getting to the point where people like the show-room new 1994, jet-black CC DRW pulling in the CG. It's a "classic". I get lots of compliments. I would take it anywhere with no concerns.
I guess all I am saying is older is not necessarily a problem. It depends, of course, on the maintenance history. Aside from that, I wouldn't shy away from it.
On edit: Just looked at the pictures. That is a pretty truck.
Manual windows - LOL I bought a used 2001 Malibu with manual windows in 2007. My kids had no idea what those "things on the door" were when we test drove it. Couldn't stop laughing.