Given the cracking I'd shy away from that 0.060 overbore. You have to consider core shift when it was cast, and some places are thinner. A good shop will know to test for thickness and voids with ultrasound. Really, I'd tell them take the minimum amount out as possible to correct the cylinder bore. The shop will have an idea of how much that will be when they inspect the block. Then you can match the pistons. The power comes from the stroker kit. Bore nah.
One thing I've noticed is the bigger is better crowd tend to end up in a mess. Take LS people. They get a 4 inch stroke kit instead of 3.9 just to be able to tell people "It's a 408 stroker". Yeah that's nice, but they end up rebuilding at about 15k miles because of the way the piston skirt comes out of the bore at the bottom of the stroke. Then there's the people who get these .600+ lift donkey dick cams on factory setups and waller out their valve guides because it's only meant for .551 lift on factory rockers.
There are other ways to make power. I've outrun a few of those .600+ lift guys with my baby .525 hot cam. Coming up on 90k miles on the build trouble-free. It's all in the details. If I remember right your intake setup, tb or manifold, was a pretty big restriction. Also, definitely invest in a nice windage tray. Think about a good modern style coated skirt piston that takes a thinner ring pack (Might require a longer con rod though, so maybe not. Budget considerations, too.). If you're using MLS gaskets specify the correct RA for the deck and heads. We've been over setting the valvetrain up for the valve tip wipe pattern
Which was a hilarious picture btw haha