I have had all of them so I will impart a bit of wisdom.
1995 F350 Powerstroke. Short cab, long box. This was a standard XLT trim truck, meaning power windows, locks, premium bench seat, shift on the fly 4x4. Dead nuts reliable, cheap parts, comfortable, looked great, and didnt rust bad. Engine-wise, all Powerstrokes 94-03 are really close. I didnt keep it long because I couldnt afford it at the time. Old body style (OBS) trucks are tougher to work on than 99+ trucks due to packaging.
Few years later I had a 2001 Chevy 2500 HD Duramax as a company truck. Short cab, long box. Low miles, 80k when I got it. Definitely car-like and enough power to move a house. It was all stock and very reliable. I think the guy I work for has 125k on it now, it doesnt get driven too much, he mainly uses his Kodiak. The interior was a big step up from the Ford.
Next up was a 2000 (OBS) Chevy K3500 Extended Cab Long Box Dually with the 6.5 in it. It ran well, when it wanted to. I made a mistake of buying a rat, and had to do a lot of work to it. Replaced a lot of interior and trim bits which was easy enough, did the brakes and front end, then it dropped a cylinder. I rebuilt it in my garage and drove it for 6 months then sent it down the road. Had a great interior when I was done, comfortable, looked nice, and ran down the road well. There is not a lot of aftermarket stuff for the 6.5, they are pretty maxed out. I have a good friend with a 1995 K3500 short cab long box single rear wheel that he bought at 100k with popped head gaskets and cracked heads. A friend and I went through the motor. New injectors, turbo, $800 worth of machine work on the heads, glow plugs. Put it back together and he has another 150k of total neglect on it. It gets worked hard daily, always starts without being plugged in, runs on soy, fuel oil, farm diesel, anything that he can get into the tank. Still running the original trans, high pressure fuel pump, timing chain, etc. We have done 2 new vacuum pumps and a rear end in it. Otherwise its a solid truck. It doesnt have as much yank as a Powerstroke or a Cummins, but it still tows a big gooseneck loaded down, but at 45 MPH.
Next truck was my 1996 Dodge Ram 2500 extended cab long box 4x4 with a Cummins Diesel. I loved this truck. I bought it from a guy I used to work for for $3500. He had it since 1998 and 60k miles. It was rusty, interior was trashed, and the front end was loose at best, but it ran great. He had put a built ATS transmission and torque converter in it to the tune of $5000, and it shifted like a race car. I pulled a complete interior from an 80k Cash for Clunkers V10, put that in, had it bodyworked, and drove it. I lifted it, cranked the pump, 4" exhaust, BHAF, etc. It was a great truck that only left me stranded when a water pump blew up. 20 minutes and 2 bolts later and it was back on the road. It was easy to work on, had tons of power, but a Dodge is definitely a step backward in interior and driving compared to a Ford or a Chevy. Eventually the tin worm got it, the frame was rusted to the point of being soft. I sent it down the road this fall before the salt hit. I didnt know if it would last another year in the salt. The floors were bad, the frame was weak. Gone at 260k.
Right now I have a 2002 Ford F250 4x4 crew cab short box with the 7.3 Powerstroke. What a great engine. Tons of power, great user support, and pretty good on fuel. I see 16 MPG in mixed driving. This truck has 240k on it but looks and runs like it has 40k on it. The interior is nearly perfect. Paint and body are a 9 out of 10 because it came from Florida and has never seen a winter. Its got the Lariat package, so full leather and power everything. Its very comfortable, and the interior is very modern compared to the Dodge. It is all stock for now. Starts even in the dead of winter without being plugged in. The Dodge took a lot of cranking to pop off. The Powerstroke just starts. Probably because it has glow plugs instead of grid heaters.