You need to ask on the V8 Board. The later flatheads would easily go out .187", so I would think the 221 would also. I know they used to bore them to 239 specs (+.125"over) on a regular basis.
That is hard to say, they had a problem with core shift on some of there V8's.
I just bored my 239 .125 because it had water in the cylinder at one time. One cylinder went into the water jacket. I put a sleeve in it to fix that problem.
You might want to take it and have them check to see if there is enough to bore the amount you want.