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

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. 

Consider partnering up with someone for your first deal. 

Your LenderMy recommendation to find numbers 2 & 4 would be to go to the top of this page and client on AGENTS  & LENDERS from there you will be connected with 3-5 pros and I would suggest picking someone who has the most reviews or most forum posts.

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

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?