Correct me if I am wrong but Joe Schmoe with no experience and no education can call himself a financial advisor.There is no governing body that administers the term 'financial planner' so I put litte weight into that title / profession, whether it is fee based / non-fee based. 

"That" alone (the age of it) may come into play soon, as most ins co's are getting very tight on the coverages and policies.Without seeing it, but knowing the climate, I would lean towards replacing the roof ... with a decent but not high end product.

Books like Fooled by Randomness make it apparent that you see a lot of sucessful people on social media, books, etc; not the graveyard full of dead bodies/failed investors. 

But lean on what other investors in your market are doing.  

Lean on your local investor network for support, and don't hesitate to seek legal counsel if needed for insurance disputes or liabilities.I hope this helps provide a starting point for dealing with this challenging situation.

Obviously you would be first position lean holder on the property.

I've done a few deals on my own in and around Detroit, but I've had to dial my investing activity WAY back due  to my W2 and other personal obligations, so I'm now leaning heavily on the skills & knowledge that the Upside team brings to keep building my portfolio.This has been a fun thread to read and I love seeing the positive rapport that they've built amongst their investors.

If you have any lending related questions, always feel free to lean on me for help!

I was leaning towards purchasing a duplex or single family home to do STR.

There is both great cash flow and appreciation markets within ChicagoNow with all that said Chicago FOR SURE has it's challenges, but I have found personally that if I lean on #1, my network, that a lot of those high risks go away or can at least be mitigated.