440 problems/quenching?/advice needed

10.16:1 on 91 octane should be fine I thought. People in Oklahoma claim that they can safely run 91 with 10.75:1. Now, I take that with a grain of salt of course, considering that most of the "built cheby's" here are junk thrown together... Cause " theys all the same"....

Now, my plan is to actually measure everything. I am quite sick of going into this blind. If what you are calculating is correct, my assumption is that that compression is with the .43 head gasket? I will more than likely be running and thicker gasket to avoid problems with running pump gas. Even though I live less than a mile from my local drag strip, I am NOT down for $9 a gal for race gas.
If for whatever reason you do wind up with a detonation problem you don't need race gas. Use a premium brand octane booster like Klotz , Torco or one of the other premium brands. Don't waste your money on parts store crap like Turbo 108 or other brands they have in Pep Boys or where ever. The of the shelf products are very weak and only raise the octane by points of a number as in .1 unless you use a very high concentration which is expensive. The premium brands are much more potent, better and easily raise octane by whole numbers. I use Klotz KL 628. I buy it off Amazon for $55 a gallon and mix it one ounce to a gallon. That's only 43 cents added to the cost of a gallon of fuel, much less expensive than race fuel including 100 octane unleaded some gas stations sell. My engine has over 11 to 1 and 210 psi cranking pressure. The Klotz works perfectly. Also you mentioned talking to Hughes Engines. I've never dealt with them but I will say that I've learned to be very careful about getting advice from parts vendors. Remember they're in business to sell parts so they will often tell you that what you have is no good and of course they have the parts to make it right. I'm not bad mouthing Hughes just stating the obvious. Good luck whatever you do and keep us posted on how things work out.