The amount my tenant is paying me per month only cover 95% of my mortgage, HOA, and taxes. 

Probably,because they need to get their tax dollars. 

That being said, there would still be income tax liabilities due to withdrawing from the retirement account after 59.5, and a lump sum withdrawal like that would probably lead to being taxed at the highest marginal tax bracket due to it being 1.5MM (this was not mentioned in the recommendations).

Highly pressured sales tactics at there 3 day events they do all over the US to get you wrapped into their high dollar coaching programs. Then when you don't have the money for them they coerce you into getting credit...

Also, you don't want to lose the tax free gain on sale. 

The wife did his tax return in 2018 Gross $120k.

So the monthly rent payments received will not cover mortgage payments, insurance, property taxes, repairs, maintenance, etc, and to avoid default the owner will be required to “come out of pocket” for the negative difference. 

From my understanding, I have to get an assignment contract (preferably from a lawyer) and sign that with the buyer.

For primary residences, lenders typically don't require PITI (Principal, Interest, Taxes, and Insurance) reserves beyond the down payment and closing costs.

However, you could still have - cashflow on paper, but still break even or potentially have + cashflow on your taxes.