We’ve decided it may be wisest to see what you all think with you’re personal experiences bearing in mind our strategy.

I could be wrong but I think in IL  or Chicago the deposit has to go into an interest bearing account and if they are due the entire deposit back they get it plus interest..

Bear in mind that business related expenses may be offset whether or not it is in an LLC.

Bear in mind these were typically short trips and by that I mean overnight to 3 weeks. 

Three stories, six balconies, center load-bearing walls, etc.

Any idea where a good starting point would be? Are

-Removing the suspected non-load-bearing wall portion.

I like to follow rules, but I'm starting to see why so many just don't poke the bear in some cases, truthfully these officials themselves don't really want/need to know EVERYTHING.That said, after informing the STR ordinance enforcer of what the zoning/permit rep told me, which is basically despite the language they have no way of tracking that nor do they really care, she only cares about setbacks, etc. not usage, the STR ordinance enforcer told me that they would give us a permit to use one of my options as an STR.HOORAY!!! 

Joe,As long as you have a scope of repairs, can use a tape measure and can multiply you can get a HomeTech book (google them, no available in stores) and use it to get a bearing on your estimates.

I'll be honest, traditional financing is going to be a bear for you right now.