I choose to use Zillow for contracts and billing and I can still do that. 

If you do choose to invest out of state, the best advice I could give you based on what I have observed running a local real estate group here for over a decade is build your own team.

I'm choosing to house hack in another expensive market (Nashville).

Call 3-4 of them with 4.5-star rating or better, ask what their experience is and how they can help your situation, then choose one and move forward.You are in the most heavily regulated state in the country, and one of the most regulated/litigious places in the world.

It seems more your fault for choosing the "lying" contractors from the tenants point of view, if you ask them to pay up, I'm sure they would.

I’ve seen clients choose a cheaper PM despite warnings, only to deal with poor communication and headaches.

., $25 or $50)- If they use autopay for timely payments, they pay just the base rent ($1,000)In the above example, you see that a discount of $25-50 was applied in the case that the tenant chooses to setup autopay to schedule on-time payments via a given PM software.Please let me know if any software comes to mind and also any feedback on the positive incentive idea.Thanks in advance!

I cant comment on the local markets, etc, but I would choose Cleveland for the simple fact you live there.

Make sure the lender you choose has a strong background in this type of lending...check them out on Linked In to see their experience level.

It takes some sacrifices; but it also takes some sacrifices to not have real estate or own rentals.... so you just choose your sacrifice!