I'm a big believer in a 1/8" overbore on a flathead that will take it. I believe the early Mercury's are in that crowd. For the cost of a set of pistons, you get 258 ci (3 more than a Merc crank). If Ford thought a 255 was enough for a heavier car, 258 should be a good improvement for a stocker. I have done 3 engines (all 8BA's) with the 3 5/16" bore, and all had plenty of cylinder wall left. Let's face it, with the way these cars are used these days, only an infinitesimally small number of them will ever need a rebore. Sure, a few may need rings down the road, but that can be done that with just a hone job.
If you need pistons anyway, why not get the extra 19 cubes for essentially nothing?