I want to buy a truck to pull my new to me used 9k lb offshore boat towing up to 400 miles each way, and to go hunting so likely want 4x4. I had a 2019 RAM 1500 5.7 w/ 3.92 gears that I recently sold as I cover 5 states for my job, and I was getting killed on auto mileage reimbursement. I feel that truck would have done ok for what I need now even without 4x4, but it was not sustainable for my job. I want something that will likely sit for days to months unused, diesel seems forgiving vs gas w/ 10% ethanol sitting, and they just pull better with the high torque. I can wrench on anything as I build my own engines, but have no experience with diesel other than maintenance on my dad's backhoes non turbo ranging from 70's to 90's models growing up for his plumbing business, and my 83 Mitsubishi 4cyl turbo diesel I drove in highschool and college doing regular maintenance, and had to pull the engine to replace the crank completely by myself when the harmonic balancer bolt came loose and wallowed the end of the crank.
First, am I headed in the right direction looking for a well used 3/4 ton diesel 4x4 pickup that I will drive long distances (to me) towing 9k lbs on infrequent intervals? Realistically I'll probably drive it 5-7k miles a year, but towing safely and making it to the destination without going into a limp mode would be at the top of my list.
Second, if that's a good fit, what's a few of the most reliable or easy to work on diesel pickups that I can delete if needed? I've seen so much put on the internet, abused tuned trucks, some of these being used for towing constantly, transmission failures, head gasket failures, turbo failures, high pressure fuel pump and injector failures, and the list goes on and on. I don't want to set myself up for failure, so looking for feedback on what year and engine to look for. In my mind, I'm looking for a very stockish 200k mile 2000-2010ish truck with regular maintenance in the 15k range that's not stripped down like a work truck. If that doesn't meet reality, should I look to increase my budget for something newer as technology marches on?
First, am I headed in the right direction looking for a well used 3/4 ton diesel 4x4 pickup that I will drive long distances (to me) towing 9k lbs on infrequent intervals? Realistically I'll probably drive it 5-7k miles a year, but towing safely and making it to the destination without going into a limp mode would be at the top of my list.
Second, if that's a good fit, what's a few of the most reliable or easy to work on diesel pickups that I can delete if needed? I've seen so much put on the internet, abused tuned trucks, some of these being used for towing constantly, transmission failures, head gasket failures, turbo failures, high pressure fuel pump and injector failures, and the list goes on and on. I don't want to set myself up for failure, so looking for feedback on what year and engine to look for. In my mind, I'm looking for a very stockish 200k mile 2000-2010ish truck with regular maintenance in the 15k range that's not stripped down like a work truck. If that doesn't meet reality, should I look to increase my budget for something newer as technology marches on?

