Used truck prices are IMHO way too high, but it is what it is. I can't stomach paying more than 1/2 the new price for a used vehicle, and by the time a truck get's to that point it's got quite a few years and 100k on the odo.
I've driven quite a few ford trucks, but have only owned a Dodge. 2500 diesel bought new in '06 and now has ~112k on the odo. It's been a relatively solid truck, I did all the maintenance and the repairs to date have been:
Water pump at 54k, it was faster to change it myself than take it to the shop.
Auto tranny started shifting weird around 90k, took it to a transmission shop and they replaced a sensor and solenoid ~$500 parts and $500 labor.
Last winter a high pressure fuel line cracked. First time I was stranded and not too bad of a repair ~$250 parts and labor.
The biggest repair was just last week. The one weakness of the dodge trucks is the front end needs a rebuild at about 100k, and that set me back about $3k.
The cummins engine is great, highway mileage is good at ~21, towing my boat drops to ~16 and city driving really sucks the diesel and I'm in the 13-15 range.
If I had to replace the truck I'd probably go with a gasser. Towing my boat is a very small percentage of the miles I put on it every year and I can live with worse mileage on those occasions. Though going up a mountain pass at 65 and being able to accelerate would be missed.
Interesting... My story is the flip side of your story:
Being a cheap SOB, I bought a used 2006 Dodge Ram 2500/Cummins in 2011. I think it is even the same color. I bought it for ~20K with 112K miles on it.
Had to add a block heater plug (just the cord) as it was a SC truck.
I've not replaced the water pump on it, but did have to replace the one on my 04. Under $60 and about two hours, but I think I could do it in 30 minutes now.
Transmission started 1-2 hunt. Replaced gov pressure solenoid with an "upgraded" version. Then swapped back to OEM solenoid and replaced sensor at the same time, because the upgraded solenoid caused a weird "harsh downshift" thing that was annoying. ($67 for the upgrade, $128 to switch back and replace the sensor while I was in there). Maybe 2 hours per swap - including dropping pan and re-filling.
Lost a tie-rod end on Denali Highway. Awkward! A buddy came to the rescue and brought the $20 part up, and we replaced it. Saved a couple thousand dollar towing bill. I replaced the rest of the tie rods/ends when I got home, and want to say I ended up spending $600 more in parts and most of an afternoon on my back in the gravel.
What all was included in your front end rebuild? I know Dodge likes to use a weird hub/bearing deal that is expensive, but haven't had to mess with them...yet.
I'm at ~143K. I'm sure I'll be building a transmission before too long too.
To the OP: I am a cheap bastard, so tend to look used and tend to walk away from deals if I don't like the deal. I've never put much faith in dealerships and less in warranties. There are tons of used trucks out there - if it looks used up, it is very likely used up.
Diesel was a must-have for me. I can't stand chevy's, didn't want to play in Ford's 6.0/6.4 minefield, and couldn't afford a truck new enough to have their 6.7. I looked for: 5.9 Cummins, quad cab, long bed. Would have been nice to get a 6-speed, but I'm happy with where I ended up.
