How to set your self up so you can continue to repeat the process with the least resistance as possible when buying your next property?

Debt on level of juggling flaming chain-saw's.... 

I own my home so house hacking is not an option, but if the house hacking can be applied to a second home that would be an option, in that my wife need an office now.and yes, the rent increase may compensate the mortgage rate but there will be a rent control or cap, perhaps 4% a year which will take a very long time to get to the massive amounts of equity and cash flow, and how I manage/jconvince/retain the resistance from tenants who definitely won't like the rent increase?

Invest where you have connections first - it will provide a path of least resistance and build a business that you can duplicate to a different market when you are ready. 2.

Ensure it's a high grade product, "Water PROOF" (not water resistant which many are) and I also caulk along the bottom edge of the trim/baseboards so if water splashes/leaks you'll see it on the floors as it pools up. 

Resistance is futile.

I am just saying you're going to find it difficult and sometimes it is best to take the path of least resistance.

@Charles MooreIMHO, majority of BP user will flame me but I have a full time job and not looking for another one to look for needles in the haystack.

The City is very resistant to changing zoning or allowing exceptions especially in the SU zoning.

I still need a vacation every 3 to 6 months and exercise multiple times a week to clear the mind.Even if you love what you do if you burn candles at both ends you will flame out.