We’re weighing whether to leverage our funds by putting 20-30% down and financing the rest, or to buy properties outright in cash and then pursue a cash-out refinance.I wasn’t previously aware that each person in a household can have up to 10 mortgages under their name.

There are a lot of ways to crash and burn, so increasing the odds of succeeding long term should be your highest priority. you can always sell your local assets once you're comfortable managing rentals and ready for a market that better-suits your criteria. btw, kudos for being self-aware of your limitations.

Working with the city to find a solution.There is a similar situation near me where an investor bought a short term rental house, rehabbed it, ran it for a while, and then got in trouble with the town after a neighbor complained and the town said short term rentals weren't allowed in the community. 

We have had rental properties where the HOA had a community pool, that was ok with me.

That way you know they are active in the BP community!

Not to mention, they weren’t aware of my entity information and other organizational details I’d previously sent (ie state formation, scope of work, etc.); easy stuff.

.), and continue to educate myself on NOI, Cap rate, cash-on -cash return etc.BP community, I am open-minded, willing to take initiative, always willing to be taught something new, but also ready to share any experience or knowledge I have that can help someone else. 

I have already sold by owner and am well aware of 1031.

Hi Jimmy,Welcome to the BiggerPockets community!

I find condos/townhomes to be easier to manage out of state because the HOA handles a lot of the maintenance, just be aware of condo fees and find a place that is reasonable like $300-400/mo or less if you are lucky.