I've been researching and viewing properties throughout the South end area and a little bit on the North end. 

Difficult to tell from the website exactly what type of Passive Investments are available: Fixed Term or Open-Ended.

Did you end up flying and looking in person in the area?

The auction is open until the listed end-time.

I went to the city and they verbally told me it’s ok to turn it back into a duplex.

And this adds up quickly since the IRS makes you pay that depreciation back when you sell.

We simply include the tax on the invoice sent to guests, which makes it easier to track and ensures we're covered for tax purposes at the end of the year.For Chicago, I’d recommend checking directly with the city’s tax office or a CPA, but generally, you’ll need to register with the city, collect the hotel tax from guests, and remit it on a regular schedule (likely monthly or quarterly).

During the "fix up" process, you would use a different kind of loan that will end up converting to a DSCR loan once you have tenants living in the unit(s).So, I would need to use maybe a construction loan for the renovations and then convert it to a DSCR loan?

You may have to do one as part of the loan process and I wouldn't want you to end up paying for 2 appraisals if the lender doesn't take the one you ordered on your own.

If you have someone reserve a year, you can charge back utilities but it might be a lot of hassle.