obrien-
How deep is the lower unit now?
You can raise it to where the top two water inlet holes are out of the water when on plane.
Do you have a water pressure guage in the boat?
Just keep raising until you notice the water pressure drop, then lower back to the previous setting.

I am assuming you already have a jackplate on the boat.
If not, you will need a ton of setback on that Checkmate. 15"-18" or more.

The Bob's nosecone really only helps on boats above 80. It will let you run a higher engine height and a air out the prop though.

A chopper would be a good choice on that boat, it needs to get the bow out of the water.

I have a 26 pitch chopper you could try sometime.

If you want to sell that boat, go register onto the forums at www.screamandfly.com . That is the mecca of outboard high performance.

Here's a pic of my ride-