Are there any consultation services (free preferably) that can kind of walk you through some of the process?

I left my job at a top strategy consulting firm in NYC to do this full time, so I have had the time to think (probably too much) about this.I have a strong opinion on the cabin rental programs-- for instance- I closed my first cabin on July 2nd 2018. 

@Brian Van PeltThank you I’m consulting with my attorney.Tenant does not speak English son is the contact person and he sent by email.

You will want to consult with some lenders to discuss their terms.

Your wife is more then likely the ‘voice of reason’ consultant.

If you occupy one of the units, then that portion is treated as primary residence and follows those laws.Ohio has the RITA tax so make sure you consult with your CPA on those matters.

So it's on you not the lender.Most lenders will do 90% of purchase price, 100% of rehab but you'll need a scope of work and a draw schedule so you need to consult your General Contractor who needs to be licensed and insured.You will need to show reserves, be an entity so LLC or Corporation and have a business bank account. 

Among others things, I have worked at NASA and currently consult for Missile Defense and DoD industrial base.I’d like to invest in the local community since I know it’s a pretty awesome place to live, work and play.

But if I wanted to try renting it out on my own is there a consultant type service where I could a knowledge expert walk through my house with me letting me know what upgrades are likely necessary and what would not lead to actual value. 

I am an investment consultant and have provided RE consulting services to a number of clients.