I just tried the oldest commit again and it seems like I tried connecting too early last time. When I wait until the save selection screen I still get the connection timed out error. As soon as you reach the title screen it becomes in possible to connect with any version of the installer, pretty sure @.44 Magnum has tried every commit available
I've also tried to connect at different intervals. I tried connecting at the title screen, the load save file screen, and after the save had been loaded and I was able to control Link and sadly, nothing worked.
On a side note, during my testing I discovered that some codes for Wind Waker HD (infinite health/have specific item) stopped working on versions of tcpgecko.elf that has the code handler integrated. Switching back to an early version of the elf before the integration corrected the issue.