Well last night I got some meaningful results, I stopped sending infinite amounts as fast as possible, and put a counter in so it only sends 5 characters at a time. It also sends 5 different characters (0x41-0x45 or 'A' - 'E') and guess what I saw?

The bus pirate showed me receiving stuff that resembled what I sent (it was reversed nybbles but that's fine, I can fix it if I need to) So this weekend I will build my breakout board and start using "sump" as a logic analyzer and get it fully tested, I can see this getting to a working state in the next few days.