I can not qualify for a long term loan until March of 2020 since my debt to income will be too high. I will have 2 years of commission under my belt at this point and will be able to qualify for conventional financing...

It's nice to know that so many people live in an area where if a contractor you don't know tells you he's going to renovate your house in five days, you can count on it being done and done right in five days.

I have learned to count my money once a year, not once a week.

That's what I was counting on and then I did a quick look on credit karma and my credit score dropped 200 points. i don't think they will make me wait due the time they've been rented.

He might offer to put up some of his own cash in the deal but I wouldn’t count on it.

I put a small downpayment in and took a private loan (for the 25% ownership) from them that I'm paying back w/ interest and somehow we structured it to count as income for them produced by this same property...

1) I use 3 times the rent to be eligible to rent  this is a HARD number and I don’t go below it ever  because it is 1/3 the gross salary of the individual which is customarily the amount recommended for owning a home or any budgeting classes or lecture or anything   So for me this is the pass fail item   If I can not verify the amount then it doesn’t count as income  2) I use 600 for a credit score minimum in my advertisements, however my tenant pool is typically 525-600 scores.  

If you are the majority owner of the LLC then that should count as your seasoning. 

I wouldn't count on the payments making you safe.

The 50% rule includes the property tax and insurance in the 50% (everything except debt service) so you appear to have double counted the property tax and insurance.