It was an adorable four square style home with 3.5 levels of living on the NW side of Chicago, on a somewhat historic block, right near a rapidly developing area.

But either way, I agree with finding out market rent/vacancy, historical operating expenses, current lease terms, (what type of lease/where they are at in the lease ect.) 

While I agree that customer staples are somewhat recession resistant as well, I definitely concur with this ranking that RE beats it out, since typically during recessions people do still need to buy staples but will still usually decrease the AMOUNT they're buying (cutting down their consumption, making things stretch further, and not "stocking up" as much as they would in non-recessionary times such as only buying 1 stick of deodorant at a time instead of buying 10 at a time), so demand and gross revenue for these products will see a temporary decline during recessionary times moreso than RE historically does.

My friends live in a historic house like that - gas bill in January was $500+. 

I have just acquired two multi family homes in the historical district.

I lived in an area with beautiful historic architecture and saw it rot away for years, neglected by the very same people who scream gentrification at the top of their lungs.They want to live in beautiful areas with lots of amenities and pay rock bottom rents without any hipsters or yuppies moving in.

I called the assessors office and she said it likely could double or triple the taxes but could apply for historic exemption, but I don’t want to count on that and then be left holding the bill which would kill all cash flow.

I’m pretty optimistic but I would keep in mind crime is at historic lows right now, in the areas your looking at.   

The zoning was changed a few years ago to be "form based" which means the city cares more about the historical facade than what goes on behind it in a large part of the city center. 

Keeping an eye on the Washington Heights area, as it seems there is a ton of investing potential there.Looking for people who have street specific knowledge, a gauge on an estimated price per square foot for a rehab, or an understanding of the historical society rules with renovations.