Is there any test that I could perform that would help better understand this problem and possibly help alleviate user error?

The JDS will show codes, but I think it is its own proprietary codes. I can send some to you in about 2 hours.

I feel when I am learning an IR code, if I hold the original remote button down longer it works a little better. I wonder if it has something to do with a “Release” function as you mentioned. Maybe the TV buffers IR commands and the buffer is getting filled. This might explain the activity, but I know nothing about how TV IR works and if this would even be a common practice.