But you might want to be extremely careful with a deal like this.

First, Chicago is extremely tenant friendly, so if you are investing in C or D areas which can only attract poorer credit, lower income or subsidized tenants, you WILL (I promise) have problems with getting all your money, property maintenance, and lost rents.

Maybe I need to think about it more, but I honestly can't think of one benefit of doing this. 

Any other advice would be extremely apprieciated!

Those familiar with the local market ( @Chris Martin, for example) know that, in reality, it is extremely difficult to find properties that hit the 1% rule in Raleigh - at least for properties outside of war zones. 

To be honest, I've never encountered the scenario.

Ours is in an area that is primarily summer only but with continuous improvements and a good rental manager our utilization is increasing into spring and fall.Best part about vacation Rentals, no concerns about evictions.Worst part, extremely hard to cash flow with traditional LTV rates.

few things if this guy is a loyal repeat client HML will many times work with you.open honest communication is appropriate.. all they can do is say no

Honestly, those are sufficient enough....I received more calls than I could handle (a bit overwhelming lol)

Honestly I thought that was the norm until this post.