After 2+ weeks of battling this challenge, I have conquered!

Issue #1: Trying to shove 247 bytes of data through a 64 byte Endpoint.
Fix: Restructured the Send/Receive from lots of variables to a 64 byte packet. The packet can be structured any way I need.

Issue #2: The HIDmaker-generated code for Sending Reports had a glitch.
Fix: I found it & fixed it in my code. I notified Dr. Bob about the glitch, hopefully it will be incorporated into his current releases and any updates he issues. I'm madly in love with HIDmaker, but it isn't quite perfect.