Take every bit of negative advice about a diesel and throw it out the window. The whole "they don't like to sit" or "they don't start in the cold" is advice from 1975 and it is completely untrue these days.
A diesel represents an awesome investment if you get the right one. Buy a gas truck for $4000 and you can sell it 5 years from now for $500. Buy a diesel for $8000, and chances are you can sell it in 5 years for $9000. Yes, you'll have to do a fuel filter more frequently, but they are $10 and they're right there in the engine bay. Oil changes usually require more oil, but these days they are no more frequent than a gas truck. More than worth it for the reliability, long life, resale value, and double the torque. The 50% better fuel mileage isn't a bad thing either.
LBZ/LLY is the duramax you should look for. They are the 06/07. You can go newer and enjoy more refinement and power at the expense of MPG. Starting with the LMM in 08, they got the DPF and MPGs went from (not kidding) 22 to 13. Having said that, the later 6-speed Allison is a REALLY nice box with better flappy-paddle (well, pushbutton) shifting that actually works. The 5-speed Allison is still great, but it is a bit of a blunt-force, old-school transmission. A wonderful box, but if you're really going to tow with it, the upgrades to the controls of the 6-speed are really nice.
Dad owns two Duramaxes; an 04 LB7/Allison 5, and an 08 LMM/Allison 6. The LMM gets used about once a week and even though it is 13 years old, it only has 35k on it. It is a sexy dually crew cab with all the bells and whistles. The LB7 is a crew/short 2500, and is abused daily. It is the farm truck, it has 180k on it of hard, heavy towing and off-roading up to 13k lbs, it has been modified with 30-over injectors, 5-position chip, intake, exhaust, lift pump, and EGT gauge. It puts 938 lb-ft to the wheels. Both are bulletproof, start just as easily in the summer or in 25-below winter, and even the owner's manual says to change the oil every 7500-8000 miles. They take 12 quarts IIRC.
I have owned two Dmax, three powerstroke, and one Cummins. They are all great with some caveats.
Dmax: Early LB7 is fantastic, but they had injector issues. 99% of them have been replaced and no longer an issue. Single-geometry turbo that is very well matched, and will likely give you 500k of trouble-free use. Since these are early 2000s, most are getting really long in the tooth.
LBZ/LLY solved the injector issues and added a VVT Garret turbo. My favorite.
LMM/LML added the 6-speed Allison and also added the DPF. Super-refined, great to drive, if you can tolerate the reduced MPGs
7.3L Stroke: One of the most reliable pieces of iron out there. Most are really long in the tooth and good luck finding one for non-crack-smoking prices. I've owned two, one of which went 260k miles only having to replace the glow plug relay twice for $36 each time.
6.0L stroke: If they have been "bulletproofed" they are surprisingly awesome. The 6.0L block is the go-to for performance builds after you've solved the EGR and oil cooler failures. Because of these failures, they tend to keep the resale a little lower.
6.4L stroke: great, but a bit of a forgotten, middle child.
6.7L stroke: Yummy, but expensive.
Cummins VE: Early 5.9 with a VE rotary pump. We're talking 80s stuff here. Bulletproof, but slow
Cummins P-pump: through mid 90s. Best one in my opinion. P7100 pump was easy to modify for power, but things were so bulletproof because they had no electronics.
Cummins 24v: late 90s until the 6.7L came out. Great engines as long as you put a good lift pump in them. The factory fuel pump failed somewhat commonly which starved the injection pump and killed it. At $1400 to replace it, a $300 aftermarket lift pump is solid prevention.
My dream truck is an OBS Ford F250 (pre-98) with a Cummins P and an Allison 1000. Those are the best pieces IMO. For my applications, Ford did the best frame/axle/body, Cummins had the best engine, and the Allison is the best trans. What I usually end up with is a Chevy diesel, mostly because the Dmax is 95% as good an engine, and the truck is 90% as good as the Ford, and it gets me the Allison without custom hacks and big money.