There are SEVERAL topics on this subject in the swapped engines forum.
Your 1988 shares essentially the same issues as swapping a 4.0 into any
2.9 powered '86-88.
It's possible, is it possible for YOU?
I have no way of knowing.
5.0's aren't as easy as a 4.0 and finding a "good"
5.0 probably isn't as easy as finding a good 4.0, as there are plenty of explorers with perfectly good engines sitting in junkyards because their A4LD Died (for the first, second or third time)
Or like I frequently find here in pennsylvania, a perfectly good RUNNING explorer that was junked not because the engine or trans was bad, but because the vehicle would no longer pass PA inspection, we have a rust law.... No perforating rust in the sides of the vehicle that produce a hole bigger than a quarter (potential sharp edges)
no perforating rust at ALL in the floor of the vehicle (possible route for exhaust to enter tha cabin) and Explorers typically self-destruct in the rocker panel area due to corrosion from road salt.
Frankly the main thing that goes wrong with 4.0's with less than rediculous miles on them is the pushrod tips gall into the rocker arms and that is easily fixed.
AD