Have you decided on which market you'll be investing in and what strategy you'll use?

If the lap, you might just be acquiring to acquire and it could be a headache to move and get going again.

Here is an update : https://chicagorealtor.com/advocacy/advocacy-resources/northwest-housing-preservation-ordinance-issue-summary/The DOH has posted the forms required to be in compliance with the ordinance which means any properties not under contract by 11/9 will need to be pulled off the market and 30-60 days notice must be provided before listing.  

Given it is straightforward, non-payment you might as well do it yourself, come to the hearing with all your paperwork. 

Typically what we look for in a borrower is someone who has a good track record, (at least 5 in the past year) along with purchase HUDS, statement of work as well as sale HUDS.

Your first trip should be to the Planning Dept and ask if it's possible based on the zoning, and if they would view it favorably.

I may be wrong but I don't expect values to go anywhere for a while.

You need to learn to be an expert in some source of stress at finding, filtering for (a data source tool like propstream.com) or buying from a data vender who is good. 

It doesn't feel right to take a monthly loss on an investment property but it could be worth it for the short term. 

A small amount of movement in the rail of a screw-drive garage door opener can be normal, as it’s designed with some flexibility to handle the door's movement.