Even though you feel you don't reach the full cash flow potential, you gain on making the lives of those families more comfortable.

Despite that, case in point- a guest decided to wash the comforter, with the duvet still on it . .. .

Choosing the best first property depends on the timeline, learning opportunities, financial comfort, and property appreciation and market demand.Good luck!

Stick to areas you're comfortable with, and try to steer away from other people's "deal calculators"; you'll overwhelm yourself.  

I'd find a mortgage broker who understands your strategy well enough to advise on products designed to help you scale. 

@Jamie Parker, most of what you'll see in the education space of REI/business is fluff and designed to take your money.

If you’re comfortable with the tenant risk and low cash flow in exchange for a solid property in good condition with long-term appreciation potential, then proceeding could make sense, maybe you you can negotiate some concessions?  

What wouldn't be better than a Roth which is tax free, has no maintenance issues, and is "instantly" transferred to your heirs upon your death (any account names beneficiaries and is transferred on death).As always, it comes down to what one is comfortable investing in, or having somebody else invest / manage for you, and what can you effectively make money.

I understand home designs are pretty expensive, and cannot just be applied to any lot/existing neighborhood.

I wont say I go above and beyond on fixing up the places and making them jaw dropping beautiful, I still do them up enough to where I would be comfortable living there.