I have a wife and 3 kids and the weight of their futures on my back.

Quality of everything is very heavily weighted, and penalized for failing at it.

Focus on the big moves: security, renovations, and cutting dead weight. 

In addition, while the umbrella did not end up having to pay out, having it meant I did not stress about it at all.  

The foundation was already approved, permitted and finaled years ago for a 3400 sf house, and its solid and I won't be building directly on the overhang edge; but rather back away from the edge a few feet to prevent any load issues all the weight will be on the longer sides of the existing footing.

I should add it will be a short term rental property. 

Once you've identified what's important and what ratios to look for to evaluate a property, all future deals should be weighted against those "good" ratios/numbers - and periodically adjust to suit your goals.

I do not see that home prices have dropped 2-3% and this is a lot of added savings in additional to a downpayment if so. 

In addition cash flow is taxed annually.  

If the stock market were real estate, you'd pay for 5 shares of Apple stock and get an additional 95 shares.