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1994 Jeep Cherokee Sport - Keep Repaired or cut our loses?

We have a 1994 Jeep Cherokee Sport, straight 6, standard trans, purchased new and is now at 240k miles. It needs some major work that has been quoted as follows: (Springfield, MO)
• Transmission rebuild: $2,800
• Transfer Case rebuild: $503
• Rear main rebuild,clutch, valve cover: $720
• Misc related: $200-400
Grand Total: $4,224 to $4,424
It also needs A/C service ($200), tires by year-end, paint (wish list), and headliner refit (wish list). Eventually we want to rebuild the engine too. We love the vehicle and want to drive it another 240k and don’t want to buy another new or used right now. Any advice or suggestions? Are we crazy to want to keep it on the road?

Any rust anywhere? Mine started rusting in front of the rear wheel arches.

The body is in good shape, no rust, never wrecked…molding is falling off but we’re not replacing it. Just needs a paint job someday.

I’d put a used transmission and transfer case in it, rather than go through a rebuild. That should save some $$$.

Why do you need to rebuild your standard transmission? And an additional $720 to replace the rear main seal and clutch when the transmission is already out is ridiculous
I agree that a used trans and transfer case would be much more sensible.

We all spend money on things that we enjoy, so I won’t tell you not to do this, but I’d say that the vast majority of people would never consider putting that amount of money into a Jeep of that age and mileage.

+1 to Texases’ suggestion.

My last Jeep Cherokee was a '96 model. I loved it but I knew that sooner or later it would need expensive repairs. I sold it and never looked back. +2 to @texases idea if you really want to keep the Jeep on the road.