How did you decide for (or against) making that leap of faith to leave the corporate world and work for yourself?

The purchase price will be coming down at least the cost of foundation work, leaving a solid 25k net profit as a sale.

If it were me, I would calculate PITI + any other costs you as the landlord would pay, then see how much that leaves you cash flowing at the end of the month. 

As for the seasoning of the title is concerned, are there any lenders that you've become acquainted with, that do not have this requirement?

We learned that when that happens, bank will only loan for value of home, not purchase price, leaving us to have to come up with $40,000, wait for sellers to come down $40,000, or walk away.

She did I have a text stating she spoke to her realtor and it was fine and confirmed I would leave the 30th of June so she could put a July 1st lease date.

So we can leave it at that.

You should have begun the eviction the process the morning after rent was due. if he does not leave at the end of the month, you will have given him 3-4 free weeks to live there.

It should definitely cashflow once you leave and all units are rented out based on current rents, not hypothetical rent appreciation in some distant future.

My biggest concern is attempting to do this whole thing with no debt.