I'd also worry about the showings and if someone steals something from the tenants.

Just because someone has a voucher doesn't guarantee we will accept them. 

But given I've paid for snow removal like once ever, I don't know what I should offer someone who is not a "pro" and already has an idea of their rate. 

I would love to meet any real players in the area who would love to pay it forward and help someone green like myself.

As far as the 1099, that is for payment to owners if you manage for someone else or your vendors whom you pay for repairs and maintenance. 

In high-cost markets like Chicago, that can be tough to meet.If you're looking at a duplex, the self-sufficiency test doesn’t apply, so you’d just need to qualify based on your personal income and the rental income your lender allows.If your current lender isn’t familiar with making FHA work in your situation, it might be worth getting a second opinion from someone experienced with FHA multi-unit financing.

Reach out to someone like @Dave Foster.

Since this is a real estate forum, I'd just clarify what someone could buy the real estate for and what your lease terms would be.How many sq ft?

You either end up doing it all yourself or need someone on your team that can do it. 

Quote from @Shawn Questa: Hi all,I am curious what some of the Pros would do to Help a Seller in this situation while making a Deal happen.I found a 200+ day old MLS Listing where the Agent said the Seller is in Financial Ruin, hasn't Paid the Mortgage in a year, owes about 180k on an approx. 210k House and multiple Buyers have backed out.I don't know how someone could not Pay their Note in a year and not at least be in Pre-foreclosure.