Over the recent years I converted it into a single-family home.

It turns out that we were never going to get paid out in the first place, and eventually found out some of my properties closed, but was still never paid out for them, but most of my properties simply just ended up dropping and i was never informed of it.

Eventually I had problems with Regions getting wires out on a timely basis.

If I was the originator on this loan (loan officer, lender, or whatever title is used), I would have made this restriction very clear to my borrower if they had explained that they wanted to eventually use the property as a rental.

And eventually or even now, go to Real Estate Events all around Chicago, most of them are free and you can find the events on Meetup.com or Eventbrite.com (my company also hosts a lot of events every month that are free @A&N Mortgage which you can find on Meetup.com).Good Luck!

I have one in Brownsburg that is similar, but there is a house and a converted garage on the same property. 

With another we're 5 building for eventual sale. 

Due to the nature of the STR property criteria in Cape Coral, it's very rare that a STR could be converted to a successful LTR.

The property sat on the market another 3 months and eventually sold for $25,000 less than I was under contract for.

I hear ya, I think the fees are negligible but I guess it would be a option not to convert or convert portion.