Feel free to ask any questions here.In addition to a "Facebook community", how about a Slack channel?

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

Still, this is a poor time in the rental season and 1 months rent can be expected as a cost of vacancy (in addition to the cost to clean and touch up - $900) .Finally and I hope this is is the last one lol - Another tenant is moving out Jan 31st and this unit also requires a full cosmetic rehab.

This is great info!

So I saved an additional $2500 in taxes after the fact.

That data would be sales price after remodel (the true numbers some agents really don't have the experience to be comping the property), the days on market you will experience (this is great info because you want to recycle the money quickly), and resources to sell the place fast not slowly which you do not want this because this could put your holding costs extremely high and push the property to little profit or no profit. 

I paid for 10k program and paying 97.00 per month for addl info needed to be more successful.

In addition to conventional loans and FHA loans, if either you or your wife are veterans, the VA also has a rehab program.I'd be happy to discuss my rehab experience both as an investor and as a mortgage broker, and at least help you think through your options. 

(G) Acceptable forms of payment of Rent (including Additional Rent) are ___ personal check, ___ cashier’s check, ___ bank check, ___ money order, and ___ the following online/ACH payment methods ____________________.

The 50% is rather deep a cut, especially with all the additional operational expenses not included into that 50%.