Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

I track the principal as a Liability account in Xero, and whenever I add it to a report, it always shows the current balance, rather than the change over the chosen time period (like with expense accounts).  

What I did get, was on a marketing email list that sells their other virtual products.

Additionally, I wanted to begin using properties to pull equity to go towards buying more.

I imagine cost of labor might be a little bit cheaper in Idaho compared to Connecticut as we ended up paying 10k for gas furnace and 5k for AC with 10 yr warranty for Lennox product.  

The founder appears to have been involved in businesses outside of real estate: ‘My dream is a locally made grooming products business’ | People | nashvillepost.comSo it does not appear there is a lot of track record there, but those are questions I would ask.

When evaluating a property management company, it's important to look beyond just the management fee and consider the full scope of services and costs involved.For example, at our company, we charge a 10% monthly management fee, a $250 lease renewal fee (unless it’s a takeover tenant, which requires additional effort to establish a strong relationship - because usually people are changing pm companies for a reason), and the first month’s rent as a leasing fee.

I agree with the others here that say you need to have some skin in the game, if you are going to live there yourself, get an FHA loan rather than owner financing, you can get a 3.5% down loan, personally I do not love these as they require  PMI which is an additional expense, and you also need  bring additional funds for closing at least for taxes, title, attorney and transfer fees . borrowing from anyone else for the down payment, to include a personal loan from the bank is not a good idea, those again will be higher int. rate.

I pull permits for removal of load bearing walls, addition of bathrooms or bedrooms, addition of footage.

Additionally, it's easy for a house on one lease to get absolutely trashed by the renter.