It can be real difficult to measure deck clearance accurately in the block, it certainly can be and is regularly done, but I think that it would be just as easy to start discussing deck heights and make sure the machinist is machining off crank centerline (as opposed to deck reference) and hitting a target number based on your measured pieces
With the 2291
Stack height = 1/2 stroke + rod + CH = 1.89 + 6.488 + 1.776 = 10.154
If he square decks it, located off the mains so they all have a common reference point, I'd put it somewhere between 10.155 and 10.160, likely 10.160 because the less you cut, the easier things fit
Now, 10.160-10.154 gives you .006 deck clearance and then you can use your common Felpro 1020 @ .041, or talk to Marc here on the forum and get an SCE small bore at .041 or wherever it is. I have some on the shelf, but I don't have the bore size and exact thickness here to calculate.
So with the 1020, and .006 below, you end up at .047 quench distance, 10.07 static compression and 7.65:1 dynamic, which is getting better
If you went with the 1020, but cut it to 10.155, or .001 below, you end up at .042 quench, 10.18 static, and 7.73 dynamic, and it's looking even better
You can stop there, what's getting you now is the long intake ramp, both options above are real good, I like the 10.155 option above a smidge more, but you could even make a little more vacuum and torque by advancing the cam to 103 ICL. That would put you at 7.78 DCR with the 10.160 deck and 7.86 DCR with the 10.155 deck
To be honest, I'd likely go with Marc's stroker gasket and a 10.160 deck with the cam on 103 for a street car, especially if it was a close ratio tranny, mostly let things fit a little better and get a little more low end for the tall first. If the owner wanted as much part throttle torque as we could, I'd do the 10.155 deck
With Marc's gasket, you'll gain compression to the tune of about a 10th, so still in the ballpark