Just remember that wholesaling is much tougher than all the gurus make it seem to be, but not impossible at all if you create the right systems and understand, when you are new, that you are solving problems, not throwing cash.

I recommend you call a local agent or broker to give you a better lay of the land so you understand the challenges/opportunities in this area.

I would also urge you to make sure you fully understand how they operate , A-Z (from how they make their profit to how many doors they are managing). 

The condo is located right near a hospital and McCormick place so we aren't do worried about it, but still a little annoying.From my understanding, the best place to do mid-term rental stuff is on www.furnishedfinder.com

Someone who is getting the DOS called is doing things wrong.The guy on YouTube doesn't understand what he is doing.

Pick up the phone or stop by local code enforcement offices to make sure that you have a crystal clear understanding of local laws and regulations.

@Steven Catudali don't understand the value that he is bringing... those are all just items you can pay a professional for. 

On the other hand, when you design strategically for a specific type of guest, they’ll not only pay your desired rate but also return and recommend your property.I go deeper into this on BiggerPockets Episode 933, but I completely understand if not everyone finds this info relevant.

I understand it become tad difficult to refinance since some lenders wouldn't lend on the home in trust, but is it easy to sell a home in a trust, just like you are buying in a trust?

My understanding is an E2 Visa is an investor Visa (ie. you need to buy a business) OR you can piggyback off an existing E2 holder.