So basically info I got at this point (thanks for all contributors in other posts):
1. Determine what options are essential and what are not for your future vehicle.
Most 91-93 models have 5.7L 180 HP V8 350 TBI engine with 295 Torque (lb-ft)
94-96 models came with 5.7L 260 hp V8 LT1 engine with 330 Torque (lb-ft)
Visually LT1 can be determined by the triangular air silencer sitting a top of the engine, if engine bay was not modified.
Earlier cars (arguably) have better interior.
Roadmasters have more standard options in comparison with Caprices (different dash board, leather interior, auto-climate system, vista roof, etc), better sound proofing.
Some cars were produced with towing package with include transmission cooler, different rear end gearing (2.93 vs 2.56) and mechanical radiator cooling fan. Visually those cars can be determined by the mechanical radiator cooling fan installed (if it was not removed by previous owner).
Cars with tow package are noticeably quicker when you drive one.