1st Gen Crew Cab Engine

I've towed with a 1992 2wd Cummins ext. cab 1 ton, at the time I had owned a 1997 1500 4wd 360 EXT. CAB SLT. Both had the factory tow pack. My buddy let me use his 92 because my 1500 had just turned 158,000 and I was towing 1000 miles round trip like I did atleast once a year and the 360 was useing major oil. I was on the road less than 2 hours and man did I miss my gas engine!!!!!!!! Lets just say that was the last time I used the 92. It was a very clean low mile truck at the time also, I was very dissapointed in that truck.

Ahh the 92 cummins(23 + mpg) is a MONSTER. hook it to anything and it'll tow it and get decent fuel mileage. unfortunately it's also SLOW accelerating as heck in stock form.

With a little bit of playing(not by adding power boosters, just adjusting what ya got) you can keep you mileage,torque and bump up the performance to rival any 360 (18mpg tops) stock gas powered truck and some 383's too. Do a bit more like a fuel pin or injectors and and it's even faster. Once you stick some weight on a gas rig the mileage goes to he$$ in a hurry, not so much on a diesel. maintenance consists of adding a bit of lube every tank for the low sulfur in the fuel nowadays to save the pump, changing the oil every 5k or so depending on use,water filter and air filter about every 15-20k or so. then doing the top end adjustment every 125k. doesn't sound too bad to me.
but it doesn't sound like you have a diesel truck to rob the needed parts from. so it might be best to go gas and live with the crappy mileage and lower towing capacity.