My technique is repeated "re-verification" on the china wall and top of cylinder between cylinders where I can measure near the deck while I go. .
If all your thrust sides are where you think are, you are good, but I have not seen a lot of side oilers that thick. If it is a center oiler with med riser heads, more likely they will be thick.
Keep in mind, no need to go a fixed overbore, torque plate hone to make sure it's straight and buy a piston for the size you need. I'd bet if the bore isn't bad it could be as little as .035 over.
Bringing the numbers you want is doable, go 4.25 arm and no power brakes, cam it healthy with compression to match and a ported single plane, it'll be a monster
Only downside is that if it is an early block, no hydraulic rollers or lifter oiling. Not a show stopper but a big hyd roller is fun and easy. Opinions vary, I am not a solid roller fan without pin oiling, so I would go big flat tappet.