I'd prefer a recommendation from someone that has been in the same boat that I am and used an attorney they appreciated.

I would love something simple and prefer a semi-rural area with at least a quarter acre, no more than an hour drive from a good-size city.

The seller would prefer to sell them together but also accepts offers separately.  

Redford, MI (B-,C, Neighborhoods)Warren, MI (C, Neighborhoods)Buy: $60k-$80kRent: $900-$1200Cash on Cash ROI: 12%-15% (Financed, Property Management, conservative savings)Cash Flow: $200-$350 a door (Financed, Property Management, conservative savings)Plenty more opportunities, more aggressive or more conservative, but these seem to fit your taste the best. 

Focusing on taking title subject to without preforeclosure is preferable. 

I prefer to send that checklist to them via email to let them know this is what I am look at, but I also walk through WITH them before they move out, so we can talk about what will likely be held back from security deposit, and allow them to address it beforehand. 

I want to work with a local owned Pittsburgh one preferably.

He is no doubt eligible for unemployment (base rate +2400/month), the tax stimulus ($1200 per adult, plus extra for kids) and I suspect that like here, groceries and more all all hiring like mad (not perhaps his preference or usual income, but an income).

I'm a Referral Agent with Coldwell Banker's National Real Estate Referral Group and I interview my prospects to better understand their objectives, their budget, their geographic and other preferences, as well as their overall perspective.   

You really need to evaluate both markets, but if both markets have had similar impacts I wouldn't hesitate to move forward with your plan if that is your preferred course of action.The current market is a bit interesting in that some people think we are in for a long recession while others believe we will bounce back from this rather quickly after this virus subsides.