I've used the search feature and Google ALOT and I'm not fully understanding how to determine what prop size, pitch and cup are going to match the motor. Is there a sheet that one of the performance mod ppl have come up with to assist?

You should talk to some of the guys who make/mod the props. Chris Courville is one of the guys quite a few people deal with. Should be able to have a good conversation with him about your needs.

Write down how it behaves and how many rpms it turns throughout the throttle range solo, and with your expected normal load, and if it rides bow high or low, etc. Send prop to your preferred prop guy (I recommend laprop, aka Chris courville). Write name and number on the prop blade, he'll call for details when he gets to it. Make known what you are looking for, ie better holeshot, top speed, etc.

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Are you in illinois buckmark. If you are who i think you are the guy doing the motor work for you will be able to help you with prop selections. And if it is you the bottom of your boat aint doing you any favors. It is beat to shit and hooked pretty bad.