I would also recommend the RPOA meetings here in Grand Rapids.

Would this still be recommended if I planned on investing in different markets? 

what markets do you recommend to look at? 

I would lean towards recommending that you pursue the deal - plus having the property remain in your family may be a net positive for you and your extended family regardless of the ultimate financial return. 

What i would recommend is joining a REA or other real estate meet-up group where you can connect with other likeminded individuals consistently and share knowledge.

Any tools, APIs, or approaches you’d recommend?

I will have a contractor do most of the work from now on Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I recommend legal advice from an attorney.

For a first time investor, I definitely recommend house hacking for most people as homeowner loans are by far the best in terms of rate and LTV. 

I recommend you do this annually to adjust for utility increases and other variables.