Newer Diesel into 1987?

[Ecnerwal]

If I put all the bodywork needed into my 1987 crew cab 4wd 1-ton, I may just choose to replace the motor (which stalls a lot per my first post, and is beginning to show some signs of wear). Right now it has the 5.7L TBI gasoline motor, and the mileage is poor (10-12 mpg highway, down to 8 around town at times).

I'm toying with the idea of transplanting a diesel, but I understand the the GM diesels of this era are not a good idea (and various price calculators show the price of the truck going down if it has one). More recent diesels raise the price of trucks they are in, so I 'm guessing the bugs got worked out. Are they at all compatible with an older tranny, and/or can a newer engine and tranny be swapped in if the new engines don't match the old trannys?

Or is this just more frustration and expense that it's worth bothering with?