I believe new construction loans typically require a 20% down payment so you'll likely need more cash on hand than buying a primary residence.

Although my cost of capital was cheap (2.5% 30yr fixed), the increased STR supply resulted in a more hands-on approach by me (better marketing, improving the quality of my check-in hose, services, etc) and this wasn't turning out to be as 'passive' as I would have liked (I've been managing my own LTRs for close to a decade, so perhaps I'm spoiled).

If you're adding a lot of value to them that really doesn't make sense for Section 8 in my mind.To be honest, it sounds like you have a large reposition on your hands and will be a difficult and long process unfortunately.

On the other hand, I have bought numerous properties from absentee owners that paid cash for their investment property here.

This got out of hand a few years ago.

I'm a local agent and investor myself, so I have a lot of first hand experience investing in this market, along with an extensive list of contractors, etc.

Unless there is money changing hands that lease is only going to cause issues for a landlord.

Do the same there and see if you find any common brokers who list a handful of the size property you want and connect with them. 

So, you are simply suggesting get my, “hands dirty,” with Long term rentals, rinsing and repeating the “house hacking” strategy before even considering STR’s and meeting REPS and Material Participation requirements to maximize tax write-offs on my future W-2, correct?

Then I usually update the financials I keep on hand to align with it accordingly.I'm a CPA but I don't even file my own taxes so please take my response with a grain of salt.