a fear I have with Air BnB is that some cities around here are thinking of banning them with absent owners.

I fear you may be trying too hard to make the numbers work. 

Hagerstown is too far out and I fear vacancy issues. 

After years of wanting to do REI, I finally really got over my fears and started learning about REI in books and mostly here on BP.

The owner, who is older and owns it outright, wants $90k for his investment, and is reluctant to finance it, fearing he won't be around long enough to see the money.   

To me there is a difference in being cautious and living your life in total fear that something is going to happen to you.

Instead of moving out they fight in court leading to the nightmare situation we all fear. 

There's not enough information being provided to the public and the media is definitely pushing a fear based agenda.

. $500/month on the property, and give us the new capital to use with other investments (we're looking at passive, multifamily syndications).In my mind, this all makes sense and we're ready to go full steam ahead...but the fear of the first time is a real thing...so basically we're just looking for affirmation that it's all going to be ok, haha.I appreciate any insight, help, downfalls, or reassurance that you can offer. 

@John Richards, It's actually a little worse than you fear.