I really see Columbus Ohio as an extremely safe bet for the next 10-20 years.

I would confirm by seeing the product then going out and checking comparables in that market that have sold. 

Chicagoland is extremely tenant friendly so understand that going in. 

. - Roof was installed extremely poorly, they missed several decking boards that were soft, shingles installed either with extreme overhang or none, 1 ft dip on one side of the roof- Lots of other smaller issuesBUT Kenny is paying for everything - the extension on my hard money loan, the foundation inspection, subsequent repairs, the roofing redo, and other things in between.

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.  

As Jeremy said, it is not just about money- the amount of extreme stress also has to be factored in.

I exclusively invest out of state (buy and hold / fix n flip) because cashflow is extremely difficult to find in this area.

Quote from @Jacob Sherman: What type of loan products are you in the market for ?  

For example, if she can't visit the property, is she good at record keeping (so everything is organized at tax time) or finding vendors, comparing product prices, finding free or low cost items on Facebook marketplace to improve the rental)3. emergency fund.

Have you ever read Amazon.com reviews and wondered how anyone ever decides which product to buy?