First of all, I would make the decision from a zero basis. 

I will ask my mortgage broker if the vacany made a difference in the final decision but I believe the decision was made assuming the grandfather status was still in place.

So my decision basically comes down to easing into being a landlord and rent my current home (est. $300-$400 cashflow) or leverage my current equity to try and get something that cashflows more and jump right into the deep end (assuming I can find a deal that would cash flow higher). 

Don't make an irrational or uninformed decision, but just be ready to act quick, making sure you have all your ducks in a row.  2) If you know you want to stay in the northern suburbs, then perfect!

Problem is that every time he tries to get a Fannie Mae loan, it seems the lenders can't figure out his financials even though we package it and give them everything they need in order to make a decision.

I wish you well but I'm curious how this factored into your decision? 

My question is I have a tenant that was given proper notice (120 days) that her was expiring at the end of June 2021; if she wished to renew her lease, there will be a rent increase ($50).The tenant responded and asked if she could have until the end May 2021 to give us her decision.

If you’re worried about tenants trying to take advantage of you living next to them just tell them you have a business partner and need to run all decisions by them.

@Timothy Hero out of curiosity, how much does an existing relationship with a customer matter in the decision to deny someone who's declared bankruptcy from being approved? 

I imagine changing it could affect my mortgage and insurance as well but want to explore all options and make the best practical and financial decision.