Ok, problem solved. So with the transom and bracket both tilting it's hard to say what dimensions will produce clearance for the motor to tilt fully up yet still clear the water. Here's a picture of the old bracket that didn't allow full upswing.
So I used the old bracket to "mock up" the transom to estimate a new bracket. A large cardboard bolted to the old bracket in the garage showed maybe 4" interference when the motor tilted up.
I wanted to give the bracket a slight tilt but concerned the motor then won't clear the water. Probably the hard part was accurately drilling the holes to match the boat because they weren't all true. Here's the final sitting position with clearance to the water as well as the transom. Success. Thanks for all the guidance you guys gave.
Lastly, I want to share this home made hoist really made hoisting the 90 lb motor a breeze. You can see we were relieved at the final resting place!