I do see his point that if you refinance to pull out enough cash to now have a $1k payment again your tax bill will be lower again now and you will have extracted equity to invest elsewhere which is superior as long as you earn higher than the interest rate you are paying. 

I extracted and copied the major milestone dates on my offer form below, but I want to make sure I fill it correctly.

The "starter house", "move up house", "mini-mansion", "downsize condo" idea is a plot by realtors and home builders to extract as much money as possible from you on transaction costs.

You have to know how to define the lands highest and best use to extract the maximum amount of money from the best buyer.Example say you get three buyers:1.

I would recommend you look at private money to help you get out of the residential mortgage and extract some of your equity.  

In practice, our cash flow is not outstanding due to various extraction of equity.  

These are not hands off options but can produce incredible returns (as of this month all our properties have had all our investment extracted and are producing infinite return).  

The high cap rate mom and pop centers can throw off higher yield but you REALLY have to know what you are doing to extract that value.

That’s a forced value creation that will far exceed any appreciation you can hope for or any cash flow you could potentially extract from just a a single family home.Plenty of opportunities here: (1) sell the lots to raise cash and pay off your loans on your existing house to get free and clear property for a long term hold, (2) Sell the front house keep the lots for long term appreciation (they will appreciate at the same rate as houses nearby), (3) Trade a lot to a builder to get him to build a small home on the back lot for you at a very low cost, (4) Sell some of these lots with owner financing for cash flow...

For example, a cash purchase which allows us to purchase at a discount that will be followed shortly with a refi to extract value and pay off the margin loan.