Bumping this thread in the hope that I can get some advice. 

One smaller note, Cook County just reassessed taxes and it's a pretty big bump (at least on my properties before I go to appeal). 

There's about $50K in repairs that should be the seller's responsibility, so now we have to decide if we want to ask for that at closing, or if we'd rather not have a retraded deal attached to us, and just bump the renovation budget from $1.34M to $1.39M.

Definitely felt my fair share of bumps and bruises along the way, but also learned a TON and am better prepared than I ever have been.

They will have one or two people that can bump your purchasing power significantly with the use of rental income derived from the property you are purchasing. 

I think I may need to bump the repair up by 3-5k though.

You could be making money hand over fist in one rental and losing most of that in another.

Bump up your insurance line-item - commercial insurance for STRs is something you'll need, and it's notably more expensive than a regular homeowner's policy.  

Alternatively, consider bumping up rents.

I dont relay understand your supposed to put fist in the address or first click on Crime?