I agree with tacojoel. Jay.....IMHO, you are at a point where you need to decide to spend the $$$ to repair your truck or retire it.
It has numerous ills ranging from suspension, drivetrain, engine to mundane things like wipers and fluid changes. My guess to make all the needed repairs it would push $6-8 K pretty hard. Regardless of the brand or make, vehicles will not run forever without repair and diligent maintenance. As the vehicle ages, it needs more fastidious and timely maintenance.
I have seen you delay repairs/maintenance until you reach an arbitrary mileage mark. This is silly beyond clown college.
Yeah, we have all heard about your "buddy" with high mileage supercharged Gen1. Do you honestly believe that owner has not kept up with maintenance and repairs????????? And how does his truck relate to yours beyond being a Gen1?
You don't like the size of Gen2. Gen3 isn't smaller, doubtful if Gen4 will be much different. Perhaps you should consider another make such as a 2WD Ford Ranger, GMC Sonoma or Chevy S10, Honda Ridgline, Nissan Frontier, Mazda B210........ Manual trans are rapidly going the way of the dinosaur. Many like to pretend a manual is a theft-deterrent. What a load of BS. Fact is manual trans have lower resale value. Sure, there are a few buyers who jones for a manual, but they are far from the norm.
Considering the extended miles you are logging, you may want to think about a Full Size 1/2t with all the comforts to make long hours in the driver's seat enjoyable. Also with a new truck you would likely reduce your stress level dealing with mechanics.