The environment closes in to naturally push us to the following step. 

Any property is subject to nature's calamities but this would not be a "random" situation but one that is going to be "sooner or later".I'd pass.

In the units that have forced air heat with ducting and furnaces (natural gas,oil or electric) we are keeping those as they are.

It does seem that a 6-plex is a natural and modest progression from your existing activities so this purchase seems reasonable.Overall there is no magic formula and every guarantor has strengths and weaknesses.

I was already disillusioned by the public school anyway, as I wasn't helping kids succeed their own personal best as I was teaching them to make neat little circles in ABCD boxes on stated-mandated tests, so I quit teaching and began homeschooling my daughter (the way a kid naturally learns) and started a transcription business.

Also you have to consider that doing the work yourself will naturally take longer than having a contractor do it for you, so you have to weigh the price of the contractor versus holding costs when you do it yourself.

My father owns a small drywall business so naturally I have done drywall with him off and on and a 2nd job, and been going to work with him since I was little.

My Dad had a pension, would have probably needed the money to last about 30 years and 16k/year (4% of 400k) would have provided more than a sufficient amount of supplemental income for him, as well as having a high probability of success based on historical trends. 

The benefactors, Land and Real Estate Owners and naturally the small business owner everyone needs around.So what needs to be done to close this funding gap?

If it is a desirable property, sometimes it may even sell at a premium due to the exclusive nature of it being a pocket listing.