As far as I’m concerned, the Monte Carlo has the same overall poor “curb appeal” to your average person nowadays as a third-generation Camaro, but with none of the great heritage or rewarding driving experience (in comparison). It was sold on the same platform as T-types, Grand Nationals, the Hurst/Olds Cutlass, 442’s, and the last (and arguably most cleanly styled) El Camino. In the grand scheme of things, this generation Monte Carlo SS was a NASCAR-purpose production vehicle with a fake Camaro nose and a lesser variant of the 5.0L V8 than could be had in the F-bodies.
With that said, I really do love the Monte Carlo. Much like the redesigned B-bodies of a few years prior (which ironically left the mid-size Monte a larger overall car than the full-size Impala) the new G-bodies came in lighter, more nimble and sportier than their Megalodon-sized predecessors. For this generation the bow-tied Super Sport was available with a not-so-super and not-so-sporty 165hp 5.0L V8 with the dreaded CCCQJ (Computer Command Control Quadra-Jet) fuel/ignition system. It’s design is archaic and finicky. Believe me, I have a very similar system on the 140hp 5.0L V8 in my 1984 Caprice. It’s one of the members of the Quadra-Jet family that I would suggest avoiding.
Barring it’s anemic (by modern standards) engine output, without all of the bullshit that comes with a fuel-injected, computer controlled engine management system, it can easily take any member of the first generation small block Chevrolet V8 engine family as a replacement with very little work. Let’s be honest with ourselves though. Chances are the common upgrades for the 305 are going to be on a 4.00″ bore block, with either a 3.48″ or 3.75″ stroke. Basically, your standard, run-of-mill, take-the-horse-to-the-glue-factory-already 350 or 383 cubic inch engines.