Part of this process would be to (re)finance the rental as an entity to keep recycling the working capital from our family property.

Recycle that list every 120 days.

I most always promote 2YL then a PC and recycle.

Then recycle.

It was 1962 & my father had some old properties down by Port Adelaide SA that we collected rent from weekly.The old bathrooms were on the outside back wall with an access door to the back yard because the external hot water units used wood to heat the water for the shower etc.The tenants had a cow in the bathroom & were milking it!!!

In my opinion, you're trying to convince the cow to either give you milk or steak.

I saw he had a truck, a good one so I told him he could go around picking up cardboard and recycling it so he could start to put together a little money.

Milking every drop out of every deal isn't my style.  

I think everything that was said about optimisation is true, but this is where it depends whether your objective is to milk the last dime out of ALL your investments or if there are some which also contribute to your own lifestyle and satisfaction (yes admittedly at the expense of optimisation).

@Rob Tossberg  Aarons Dad Bruce is a famous predictor and economist in regards to RE cycles that's why I asked.for me I am buying a home to relocate to and take up residency in NV to escape the winter in OR and take the tax advantages of being a NV resident.