Use a 95-00 Dakota bell and mount a bolt up a supercharged GM 3800 to that nv 3550.
You can get a entire second gen donor car for around $800. If you know someone in the collision business head to a dealer auction and find a 3rd gen one that has been rear ended or rolled. There is a freaking security thing on some of them but it is easily fixed if you ask around.
It is one of the lesser done swaps and stuff is out there to make it damn near plug and play. A second gen swap(entire 150k donor car, junk yard bell, mounts, aftermarket plug/play harness and all the little things that add up) you should be able to realistically swap it in a 2nd gen under 2k doing the work yourself.
The third gen is much better tuning wise then the 2nd. But get what you can afford to stuff it in there kind of deal. The amount of power and torque you can get out of a supercharged 3.8 with a few simple and mods (like a simple pulley swap which makes more boost for example). Best of all these things are like everywhere. The bottom ends on the second gen are damn near bulletproof in stock supercharged form.
Probably the best benefit is that the supercharger does not kick in till under heavy load in stock form which means "in many cases" despite needing to run 91 octane it will cost less per mile to drive then most of the other stroked engines you are considering. In stock form a supercharged 3800 will give you enough of a boost in power to make a difference while not making it at a rpm range that is going to break parts.
The only downfall of these engines is that they do not like an high compression ratio. There is really no need to up the compression though you can spline twisting amounts of power by messing with the top end alone if you decide to at a later time.
That's just my 0.02 considering reading this thread up to this point. Run what you want its your money after all. But, not to many people will look at a supercharged jeep as a bad thing.