In what ways do people anticipate these events, and strategize to maximize their returns.

You deserve to be with somebody that not only will file things correctly (there are roughly 5 issues with everything you wrote above that need to be thought through and well considered), but will also be able to help you strategize and plan as you grow.The answer is so much beyond just the 27.5 vs 39 year question you're asking. 

I have successfully met with 3 investors in my local area. Two of which have experience with the acquisition of apartments and 3+ unit properties. I have purchased my first duplex and am currently househacking it, but...

My forte lies in being a quick learner with a strong foundation in analytical and strategic thinking, skills I've finely honed through my experiences in software development.

Should I go this route, my intention would be to strategically paydown my primary and some of my lower-cost rentals to accelerate the cashflow and arbitrage the monies elsewhere.  

Do you provide strategic, Real Estate tax planning throughout the year for clients?

I am thinking of going medium term, but that's part of what I want in a property management partner is someone who is strategic in helping to figure out the optimal way of doing things. 

You want an accountant that can help you strategize and who is responsive when you want to know the tax consequences of the decisions you are making throughout the year.Good luck and let me know if you have any questions.

I like the 100% financing, still recommend keeping track of those va funding fees for strategizing - they can make a difference if you're aiming for a shorter term resale.I wish I had figured out the house hack in my younger years!

.- it's more fresh money where you could strategize more, and the money has 0 percent rate, while HELOC money is 4% above inflation.