I just passed the 20th anniversary of the delivery of my 1998.5 quad cab. I intend to keep it as I am not putting as many miles on the truck as I did in the past BUT I still have need for a 3/4 ton vehicle on a fairly regular basis.
That said, at 261,000 miles, I am finally putting in some long overdue maintenance and life extension work. Parts alone have been about $3,000 (so far) and I have more work to do. Projects completed so far are new front hubs, new front axle seals, new rotors, calipers brake pads along with front steering gear, tie rods, drag links and the like. I also placed new u-joints in every location that they are installed and had the drive line balanced and reconditioned. Even the spring plates and u-bolts in the rear have been replaced.
Next up is a new accelerator pedal position sensor, sidesteps and body work. I have already put in a new driver's seat bottom cushion and will begin the long and slow process of installing new wiring cover/protection wherever that I can reach.
In short, lots of work. If I could not have done the labor myself, I'm not so sure that I could have justified the repairs. It would be better at that point to find a more capable and newer used truck. If the truck was rusted out or badly damaged, I would not have made the effort. It really comes down to a personal call.
I guess that it is in my genes---I tend to keep vehicles a long time but this truck meets all the towing and work needs that I have. I really enjoy the 5-speed manual transmission as much of the miles are spent in the mountains pulling and descending grades.