Really would like to lock this one down, but looking to put minimal cash into this one.Even considering the thought of figuring out how to classify this as a 4-plex with an ADU, to qualify it within FHA requirements!

I have started dissecting the plethora of content on BP and have signed up to attend a local REIA here in Chicago as a first step and feel there is a wealth of information available for free or at minimal costs.  

The inspections shows LOTS of CAPEX needs, as it sounds like the last 8 years have been minimal or deferred maintenance on the exterior.

Biggest question ~ lets say we sell the primary home move into an investment and convert the investment to primary residence, what the some good ways to invest the income generated from the sale of the primary home (ideally in tax minimized conditions.).

I looked to minimize my risk in increase my potential.  

Upon re-reading my post, I realize I've not clearly conveyed the intent here, which is to minimize the amount I borrow from the local bank. 

A VA Appraisal is just that an appraisal with minimal cursory look at some items such as is the water on, turn the heat on and a ground level visual of the roof.

It is minimal enough that it could easily be resolved with a few hours of work which we are prepared to do.

Most lenders will not allow you to get a loan for the down payment because they prefer your debt to be minimal before their debt hits your credit.

The price was right, with very minimal work.