Look into Baselane it’s designed specifically for real estate investors, You get automated rent collection, expense tracking, it makes it easier to manage properties, stay organized, and keep up with your finances. 

The tenant wants to stay 2 weeks post closing in order to get all of his stuff out.

Try to stay close to the median home price for that city. 

There's a lot more compliance, regulations, and other protections that many brokers do not feel comfortable hiring just anyone. 

It is surprisingly easy to manage out of state and if you want more tips on how, check out Bigger Pockets book "30 Day Stay" on Mid Term Rentals. 

He’s also interested in staying in the home if possible and deduct the rent from the balance he owes.

That new owner then makes the payments to the lender even though the loan stays in that previous owners name. 

Even if you stay on top of it, other stuff can happen.

Lending terms will be important here.I'd say the biggest challenge thus far is making sure I feel comfortable managing this remotely, as it's located about ~150 miles east of Dallas. 

Since you’re committed to staying close to family, I’d suggest focusing on properties that might need a little work but have potential for appreciation in your market.