Theres a lot to respond to here, so I'll try to answer and explain, one at a time….
Of the alternative vehicles that you mentioned, each has their pros and cons. The trick is to find which vehicle offers more pros than cons. Here is my break down as to which and why;
Cherokee and Grand Cherokee. I'll be referring to older models, none of what I say about them will apply to the new models (And if you could afford a new one, you could afford the Wrangler) Both have solid front axles, both offer a good 4.0L inline 6. The GC also offered a V8. The GC has a little more interior room. Parts for them are abundant and aftermarket support is great. The solid front axles are good and provide excellent articulation, but they aren't super strong.
Dakota and (1st gen) Durango. If I were to go with one of these, I'd get one with the V8, preferably the 318 or 360. (Or if you go with a 2nd gen Durango, with the 5.7 Hemi V8). The great thing is prices for these are even less than the Chero and GC. But they have several disadvantages compared to the Chero and GC. First they have a weaker IFS front suspension and will require lot of custom work to correct their shortcomings. Second is they are heavier than the Chero and GC. (V8s will help offset the weight disadvantage) Third, theres plenty of aftermarket support for the 318 and 360, but hardly any for the 4.7 and nothing for the rest of the truck.
Part of the effort will be dealing with the wiring harnesses. If you want a simple plug and play cab swap, you'll need to use a quad cab, cab thats the same year as the regular cab you intend to replace. If you can't match up the year, then you'll need to swap much of the interior including the harnesses. The biggest issue maybe to find a quad cab in the first place. It took me about two years to find a solid rust free quad cab to use.
I would suggest some kind of bed. Although, the truck will be lighter without it, it's the weight on the rear tires you'll need. For me, I built a classic Power Wagon style utiline bed (Step side bed in Dodge speak) However, the shorter regular cab frame probably won't have room for just a fender and I would suspect that the rear tires will be just inches from the rear of the cab, so i would do just a simple flat bed which will also provide a space to carry stuff you'll want and need.
If you want something that is relatively turn key, I'd probably choose the Chero or GC as these are well suited to what you want and require the least amount of time and money to set up. I would consider a Dak or Dur if I wanted something I can build, like for example, adding one ton solid axles, or dropping a healthy V8 into.
Ed
Wranglers, especially the 4dr models are very popular and the higher cost reflects this. I wouldn't drop the idea, because over the next few years, the price will come down and believe it or not, most never see the dirt. Just keep your eyes out for the ones that are riding on street tires.
Of the alternative vehicles that you mentioned, each has their pros and cons. The trick is to find which vehicle offers more pros than cons. Here is my break down as to which and why;
Cherokee and Grand Cherokee. I'll be referring to older models, none of what I say about them will apply to the new models (And if you could afford a new one, you could afford the Wrangler) Both have solid front axles, both offer a good 4.0L inline 6. The GC also offered a V8. The GC has a little more interior room. Parts for them are abundant and aftermarket support is great. The solid front axles are good and provide excellent articulation, but they aren't super strong.
Dakota and (1st gen) Durango. If I were to go with one of these, I'd get one with the V8, preferably the 318 or 360. (Or if you go with a 2nd gen Durango, with the 5.7 Hemi V8). The great thing is prices for these are even less than the Chero and GC. But they have several disadvantages compared to the Chero and GC. First they have a weaker IFS front suspension and will require lot of custom work to correct their shortcomings. Second is they are heavier than the Chero and GC. (V8s will help offset the weight disadvantage) Third, theres plenty of aftermarket support for the 318 and 360, but hardly any for the 4.7 and nothing for the rest of the truck.
Cab swaps are possible. I did it myself, replacing a rusted out 99 extended cab for a quad cab. Heres what to expect. You'll have to cut, move and re-weld the rear-most body supports thats on the frame, and build two for the center mounts (quad cabs have 6 body mounts) The front mounts are fine. You'll probably have to alter, or replace the gas tank to fit the new configuration.
Part of the effort will be dealing with the wiring harnesses. If you want a simple plug and play cab swap, you'll need to use a quad cab, cab thats the same year as the regular cab you intend to replace. If you can't match up the year, then you'll need to swap much of the interior including the harnesses. The biggest issue maybe to find a quad cab in the first place. It took me about two years to find a solid rust free quad cab to use.
I would suggest some kind of bed. Although, the truck will be lighter without it, it's the weight on the rear tires you'll need. For me, I built a classic Power Wagon style utiline bed (Step side bed in Dodge speak) However, the shorter regular cab frame probably won't have room for just a fender and I would suspect that the rear tires will be just inches from the rear of the cab, so i would do just a simple flat bed which will also provide a space to carry stuff you'll want and need.
Making such a set up weather proof isn't a big deal. You can have someone sew up a nice canvas top with snaps, and rivet the other part of the snaps to the body of the truck, at the new opening. The bigger issue is you just can't cut off the back part of the roof on the Grand Chero without weakening the entire structure. The GC has a unitized chassis and the roof is an integral part of that structure. Cutting off the rear will weaken the chassis. Unless you plan to use subframe connectors and weld in a roll cage. Don't cut off the roof (in whole or in part)….. This doesn't apply to the Durango. That truck is built on a full frame and the body is a separate structure.
If you want something that is relatively turn key, I'd probably choose the Chero or GC as these are well suited to what you want and require the least amount of time and money to set up. I would consider a Dak or Dur if I wanted something I can build, like for example, adding one ton solid axles, or dropping a healthy V8 into.
Ed