Deep clean & quick rent out or something else? 

You have the misconception that money solves all problems, or at least relieves your feelings of guilt.

I personally like to throw any potential deals into a short matrix spreadsheet that I've developed over the years that is easy for me to enter and shows me things like current/max rents for area, income expenses, cash flow, cap, CoC, location rating, if they'll carry to judge side-by-side before I spend the time do a deep dive into the numbers.

Erin and I are seeing our buyers compete against multiple offers on most homes right now, and we're digging deep into our bag of tricks to make our offers stand out put the best face forward for our clients.

Doing that can get you in deep trouble.

I don't mean to say I'm a market expert or a local, but I have done several deep dives into the area. 

You definitely shouldn't have been thrown in the deep end with no support (unless you knew that going in).Your primary questions seem to be around financing.

Yes, @Mark Ainley  and I started that (assisted by @Tony Angelos) for folks who want to dive deep into the different Chicagoland neighborhoods. 

You might want to deep dive there first.

I'm not a fan of metal or anything fancy - one simple top tray with a deep bottom section is right for me.In addition to my toolbox I use a job bag.