I hope you're (we're) wrong, but my money is certainly betting against that. 

A better bet though would be buying in a gentrifying area such as West Town, Irving Park or Albany Park which may have stronger upside, you also can get a bit higher cashflow in these areas on condos.

If it was my choice I would have gone for architecture technology.

if your FIL  does not mind  I bet most folks on this site would advise you sell .. 1031 if you canand roll that up to a bigger income producing property. 

I'd rather have as little of my own money in a deal as possible, so if my only choices were 20% or 25%, I'd choose 20%, but honestly, I try to find ways to keep all my money out of the deal, period.I'll borrow so I can offer cash on a property and get it at a cheaper price so that when I refinance, even though they keep "25%" equity in the house, the refinance is on a higher value than what I paid.

I feel like I am making the right mental choices but its hard not to believe I am overthinking things.Has anyone else felt like they have analysis paralysis? 

Best bet is to have an attorney look over the contract in its entirety so you can get the best advice.

@ChristianWeber I see you have 3 choices: 1-Accept as is and eat it(not recommended)2-Walk away and learn to spot some of the issues before you pay for an inspection. 3-Ask for cash back at closing to cover things in report, start around $15k-$17k looking at your numbers.

Also, you can bet I have absolutely jotted down those resources in my collection, thank you! 

Everyone starts with no experience of course and those that have completed deals are a much safer bet than those working on their first.