Research, research, research. Type in stroker kit on the internet and talk to your local machine shop. It cost me about $700 for a complete rebuild kit for the block minus the crank. It cost me another 400 dollars to have the block decked, I had them install the new cam bearings , bored 30 over, milled the head, and some other head work done . It was just a standard rebuild and after I work out the bugs it runs great.
The reason I say research is because 1 these kits get very expensive and 2 because once you go 60 over and you screw that up you gotta start looking for a new block. I know you can go with one of the kits that require 40 over but what's the point. And also you need to consider once you go with a higher compression motor you can only run high octane fuel.
Don't get me wrong I'm all about the big stroker 6 with a supercharger & yeah you need to look that up too. I believe you're looking at about 400 hp when it's all said and done but you're also looking at enough money that you can drop in a v8. Your question is about the same as the stick or automatic trans. question. You need to figure that one out on your own because it's all about your preference for your situation. If its not a daily driver stroke it like you never stroked it before and save up for the supercharger. That's my two cents.