use a lift and transmission jack it will make life ten times easier. ive tried it with the truck on the ground and also with a lift.
on they lightweight flywheel i would be a little worried if it would handle the torque of a diesel. most aftermarket flywheels i have seen for diesels are heavier than oem

 

Yeah my valair dd weighed right around 125 pounds

 

the flywheel is heavy. I'm not real big but of decent strength and have a hell of a time getting it on alone.

 

stcok flywheel weighs about 61 lbs

 

i want to say my ofe kit was 90 pounds and 50 or 55 of it was the flywheel (separate boxes and going off memory)