I may need to target some business groups l. 

I'm in the learning stages too, so don't pay too much credence to anything I have to say :-).That being said, I'd be a little nervous about the vacancies- if you buy on actuals using 20% down, that's $31.2k/year gross minus $21k/yr (rough & conservative estimate using 50% rule-of-thumb on $42k gross at full occupancy, since you'll still need landscaping, garbage service, etc.) minus $10.8k/year debt (conservatively using 5%), which would put you at -$50/month right out of the gate.I'd probably want to see a rent roll and trailing 12mo P&L- I'd also want to know how long those two units have been vacant, and would try to find what the reason is (whether you happened to catch them when 2 tenants moved out, or whether there's a bigger underlying problem). 

It will better serve you to MASTER one or the other.

So I served her on February 3rd with a 30 day notice to vacate and she accepted.

I got my license five years ago so I can't remember how long it takes to get a seat at a testing site (if memory serves me correct I think a week or so).

Something that size, if you don't have big pockets, is usually best served in phases, where you can get some money coming in and, more importantly, people living at the site so that other people are encouraged to buy as well.

@Jen L.

Consider moving to one of the burbs that has a Metra line that services the station that serves Amtrak as well.If you desire to live IN the city, public transit is very reliable.

Also, I would consider splitting the home into apartments but would prefer not to alter the exterior of the home, which may make it difficult to split up.Are there any positives to go through a bank opposed to just paying my m-i-l directly?  

This serves two purposes.