Seems odd as this would be a business expense for my business.  

Jim's bleating about government being involved.

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

So if you are in a 30% combined tax bracket you get an additional $3K due to write offs.If it is a rental, you can write off the business expenses and the depreciation on the non land valuation. 

Beg family and friends to fund it for you.They "might" do it if they see you've learned a lot and your business plan sounds very solid.How do I know this "might" work?

I've been toying with the idea of adding an ISA to my sales business.

It's easy to bite off more than you can chew in this business and that's especially not a good idea for your first deal.

It is important to remember you own real estate in the Poconos and you are choosing to operate a STR business.

You have every right to be outraged at the offending party and that's the tenant.Stay focused on what matters and that is getting back in business. 

Everything looks great and a year later that employer goes out of business or lays everyone off?