Matching numbers is the Holy Grail of good musclecars. The Monte SS in stock form is NOT a good musclecar. In fact, ditching the 305 for a 350 will increase the car's value if you do it respectfully. If you are a hack, it will make it worth less, but the same goes for modifying the stock engine too. The biggest problem is the small bore you get with a 305. It shrouds the valves and makes it difficult to make decent power in a naturally aspirated form. Remember that in a wedge head 2 valve V8 engine, the diameter of the bore is the limit to the total of the diameters of the two valves (the actual graph would be asymptotic...). So, with a 3.75 in bore, the total of both valve heads is 1/4 inch smaller than in a 4 inch bore engine like a 350 (I forget the exact bore of a 305, but you get the point.). Expressed using limits in Calculus, you get.... well, nevermind. Calc even confuses me! You get the point though. A bigger bore is needed to let the engine breathe, and a 305 has the smallest bore of any Small Block Chevy save maybe the 262. The 350 is cheap and plentiful to find, which is why so many people build them. Is it the best engine for all seasons? No. It has it's flaws like any other engine that can trace it's roots back 55 years (or 43 for the 350 alone). However, the vast availability of cheap parts makes it one of the easiest v8 engines to tailor to your needs. So my advice is to build a low buck 350 Chevy. In the long run, your money will be better spent than it would be on a 305.