@Dan Grec I really enjoy your content and your engine swap tale was all too familiar. A lot of time, money, effort and some stress along the way to getting it where it needed to be. For your use (Overlanding outside the USA) I'd never recommend it and agree 100% with your conclusion that sticking with factory reliability is a much better path when venturing across the globe. In fact, all your common sense "don't build a rock crawler for overlanding" advice is spot on.
In my case my JKU is fun daily driver local runabout and camping / 4x4 rig and I've put the time and money in to be able to diagnose and fix (or have fixed) any issues. Definitely a "project" vehicle that will be that way from now on. Three points I'm not sure you covered that also argue against a swap are 1) you won't get the money back out of it and it will be expensive no matter how you slice it and 2) You can't insure it much beyond the non-swapped stock value so you are risking losing everything you put into in case of an accident, fire, etc. and 3) Depending on how you swap it you are deviating from the factory crash tested configuration and could have additional issues in an accident. These points apply to other expensive mods like suspension, armor, etc but in the case of an engine swap it's considered a salvage vehicle by lenders so you can't even trade it in at a normal dealership.
I'd only advise swapping if you have plenty of money, you plan on keeping the vehicle forever, and you enjoy working on and maintaining it as a hobby in itself. Think of it the same as building a classic muscle car or hot rod. You will connect with all kinds of great car enthusiasts well outside the overland and Jeep / 4x4 world (I've participated in local hot rod meets) and when setup right they can be a real pleasure to drive. By having Motech (who've done hundreds of these swaps over the past 15-20 years and invented a reliable kit) do mine in Las Vegas I ended up with a turn-key build that, other than some post-swap engine bay and exhaust heat mitigation work, has been 100% functional and reliable and runs and drives as if it was factory.
Cheers and look forward to more of your videos - they are some of the best out there!