With the money you have to spend, you could just about buy a new truck. However, with your desire to minimize electronics, that may not be what you're looking for.
Trucks from '94 to early '98 had the all-mechanical Cummins 6BT engine. Trucks in that range are going to be high-mileage, and need a good amount of suspension work.
If you can settle for a little bit of electronics, and don't mind putting a few hundred dollars into some aftermarket accessories, I think you'd be best served with an '01 or '02 truck. To get an extended cab, you're going to have to accept the four-door model (the rears are half-width doors that open suicide-style). With this year of truck, you'll have the High Output ISB engine, and a 6spd manual transmission (the NV5600). The transfer case is still manually operated, and if you desire, you can replace the vacuum-operated front axle disconnect with a cable-operated unit.
You'll have better brakes than the earlier trucks, with dual-piston calipers up front. I would highly recommend a fuel pressure gauge, and would also go with an aftermarket fuel pump setup (I like the FASS units myself - relocates the pump and filters under the bed, gives you a larger fuel filter and water separator, and lets you run a 3 micron fuel filter). The one weak link with the ISB engines is the lift pump, which if/when it fails, can destroy an expensive injector pump. By monitoring the fuel pressure, or eliminating the stock lift pump altogether, you mitigate that problem (or eliminate it completely).
I have a 1995 Ram 2500 Cummins TD, and the 94-98.5 are very impressive but maybe you should consider a 03-07 models if you don't get 4 doors you can find them cheaper. I do not like the 98.5-2002 because of the V-44 injector pump, it is just not a good design. The first of the new body style are actually coming down in price and Hop Up parts are all over the place. First look under the hood is impressive how simple they are. I drove a 6 speed and it was hard to drive around town but obviously easy on the highway. I only went 20 miles of mixed driving. For $30K you could get a nice truck and have a super reliable transmission installed (good for 800hp and 1600lb.ft) Blackbook value for a 03 regular cab 4X4 is $13K-$21K depending on the truck plus you have to add $5600 for the diesel engine. This would make buying a diesel engine on a new vehicle have no depreciation. Good luck.
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