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.
R.D., Kathy, Jonah(16) and Meg(14)
1994 F-350 Crew Cab, Dually, 460 with Banks P/P (50k miles - showroom new!)
1998 Prowler 31 5R
Money you can beg, borrow and steal, but you only have your kids for a season.