That way if a lawsuit comes down, at least in my mind, it should be more difficult to reach my personal funds.From another angle, you should have no trouble tracking the money trail in another account if needed, but gets more complicated if you include all of your personal transfers.

The former can be difficult to get in the case of deceased owners, unknown heirs, or just people who have moved away. 

I figured from the get-go that it would  be more difficult for me as a first-timer without the contacts of a seasoned investor and what you all have said confirms it, but I'm in it for the long haul so I just have to look hard and be patient.

Repairs $28,500 roughly $34k in ARV $85k Rent $875 Taxes $95 Insurance $75 Termite $50 Repairs $80 Cap.

As you know, finding good contractors is difficult.

Doing the math isn't that difficult in terms of return on investment but the biggest question in my mind is...is it worth it?

What is a good going in cap 7-8%

This makes it very difficult to qualify for an exception as it would be challenging/impossible to rent out as a "long term rental" - which I can't quite tell what is defined as.Any thoughts on strategies or ideas on how to deal with this, aside from simply selling and getting out?

A lot folks who are finding themselves priced out of neighborhoods like Edgewater, Lakeview, Ravenswood, etc are heading over to the NWside and finding good renters hasn't been too difficult.  

I meant to continue with "or move out" without me filing an eviction, which I noted would make it very difficult for them to rent in the future.