I have family at a major airline that is willing to help me get on as soon as I'm done with my training.
Did I read this correctly?
You have family at a MAJOR airline that is telling you that they will help you get on with the MAJOR airline as soon as you are done with your training (I'll assume this means Comm Instrument and ME ratings - not even any instructor certificates)?
I also have an individual who knows me well willing to get me into a part 135 operation which will allow me to begin building my flight time.
MUCH more plausible.....but still not a walk in the park.
As far as the history you gave - and the issues with the FAA - it will be tougher than the normal bear - but you won't know until you give it a shot. Do you have a plan B and C?