I've never had any RE courses from university or any other formal education so I am going into the industry with almost no knowledge.

Our house borders a wooded area around the lake so theire is wildlife around.

Blanket statements about S8 being all good/bad is oversimplifying the issue: it’s simply another means of tenants’ paying their rent and should be considered independent of the formal, written rental qualification standards every landlord/PM should have outlined well before they start showing rental units. 

First floor features living room with wood burning fireplace, formal dining room, kitchen with granite countertops, SS appliances, full bath with beautifully tiled shower, hardwood flooring and recessed lighting.

First floor features living room with wood burning fireplace, formal dining room, kitchen with granite countertops, SS appliances, full bath with beautifully tiled shower, hardwood flooring and recessed lighting.

I think that everyone's circumstances are different and you should speak with a cross border specialist.

In our situation, to get anywhere close to a decent cash-on-cash return, I'm guessing we'd have to limit ourselves to studios and 1BD condos within the city, or properties just across the border in Maryland or Virginia.

That would be a fair deal for bucktown if numbers are accurate and it's actually within the border of bucktown proper (many agents lie about this)...

The next steps I'll be taking is a formal review of my business plan and possibly my pitch deck.

Another option would be to get them to hire you on a W2 as a formal employee.