I’ve considered going with rate term refi instead of cash out and then strategically doing the cash out in a few years, more as a portfolio refinance or cross collateral move.

There are many benefits to investing strategically in the markets that offer the best returns & diversification. 

Are people potentially taking negative cash flows and strategizing to profit off appreciation?

Unless you see that increasing over time, could make sense to strategically exit your assets and put it into something with higher yield. 

The duplex is very small & some upgrading will definitely be in store but am wondering what are the most strategic upgrades or renovations I can do to increase value in my home?

I asked the owner if he needed my help and strategized with him on how to save the property from foreclosing.

Annual inspections and overhauls are costly especially with larger or older aircraft.

and how could I strategize this any better to keep only 150k initial investment as my max out of pocket with pool?

Strategically offer on properties to make it work6.

If you were a grinder willing to eat ramen for every meal and live in a vehicle, it would be an easy choice of talking to the spouse and making a plan that for ___ months your going to live a regimented life, strategically use every minute of time you have, a grind every available hour after your 9-5 at "breaking in" to what you want to be doing.