If in the quiet title process some lien holder can show they didn't receive proper notice, they can redeem, by reimbursing the actual buyer at the tax deed auction.

Because of a part-time job in Chicago (housing reimbursed by employer)  I'm considering an investment property in the area -- if for no other reason than to write off expenses, and because there are still deals to be had here. 

Is this normal or not.This terminology is what is worries me because whatever I spend for repair and is completed I expect reimbursement.  

If the landlord doesn't fix in a reasonable time determined by the court then they could tell the landlord they have to reimburse you for the expenses.If it was an immediate emergency and the landlord was not responding then a judge might deem you getting someone right away necessary because it couldn't wait for a slow response.If the landlord is not given proper notice in writing and a reasonable time to correct the non-emergency problems then likely you will not be reimbursed those costs by the court.

Or is the contractor going to pay for the materials and then you reimburse him? 

So you will probably need to have access to ~$10K liquid for short amounts of time to make payments in between getting reimbursed for them.- When you refi you will probably not be able to pull cash out so don't plan on that.

@Luke Carl I don't disagree on the likely down rank in platform algorithms and while rare on my end as well the cost of being wrong and/or the language around host concerns having to "prove" a guest will violate house rules is what causes me pause here, since anyone that's ever tried to seek reimbursement for "proven" guest damages or other items knows well where this ends up.

We've managed several properties with warranties and we ended up spending more time and money chasing down repairs and reimbursements than we would have by just calling our trusted repair personnel.

This S-Corp will be used for management and tax reimbursement.

.)- Keep track of materials purchased, at the end my contractor wanted an additional 30K to be reimbursed to him from the bid.