Not saying you should or shouldn't,just my story.
My 69 Fury III 440 is going to a mild 505 build and is designed to go anywhere at anytime. Everything is been designed to be well within the limits of the parts installed. You can build a 440 to make the power of the stroker but it will be more stressed to do so with it's shorter stroke and displacement and higher rpm's. The 505 will have good idle [not a Cuda wannabe} and vacuum but much more torque and hp to push my 4000 lbs Fury with 3.23 rear with ease. The design is said to make 600 ft lbs torque starting at around 2800 rpms. I will be able to go to cruises and putt around no problem. Mr. Duane Porter [Porter Racing Heads}who was recommended to me by
@FURYGT designed the engine after much consultation on what I realistically wanted from the car. He is a big contributor on FBBO forum and highly respected by all there. The engine will look stock and Turquoise all over . No shiny aluminum heads or intake. It will run a custom grind cam designed by Mr Porter with hydraulic rollers. My goal is build it once and enjoy till I can't drive anymore. I will say it is not a cheap project depending on how you build it. You could go flat tappet cam which could save you a bundle. Racers don't like hydraulic rollers but this engine won't see much over 5000 ever. If you don't get greedy and "leave some power on the table" as they say ,I believe you can have a very reliable stroker to drive anywhere with great increase in power that runs on pump gas. A stock 440 is reliable because much power was "Left on the table". Also in the equation it is a good idea to get a modified torque converter to get the most from the stroker engine.
@MEV told me about his setup and says you would never know it wasn't stock till you nail it. So I ordered one. I have no personal proof of all this because my project is not completed yet. But I have seen guys here and elsewhere [FBBO etc} that have succeeded very well and then some greedy ones who either weren't happy with the drivability or broke something or are forever addicted to race gas. Then there are guys that want lopey idle ,no vacuum and run race gas. Fine but I think the important thing is to decide what you want from the car then what to do to get there. Most all avenues of building these old engines are beaten paths now. That's a good thing.
As the saying goes "Different Strokes for Different Folks!"