These loans are tailored for investment properties and can help clients maximize cash flow without the typical income verification hurdles.

So unless there are big hurdles to buying across state lines, I don't really have any concerns of doing whatever I can on my own and outsourcing the rest to the folks over there. 

The main floor shown below is roughly 1150 sqft.

When I search properties mainly in Punta Cana I always run into sites where condos are in development and have about 1 - 2 years till completion.

Lender wise talk to @Zack Karp or @Jose Valdovinos...all of those folks work mainly with invetors and have a great pulse on the Chicago market.

The main disadvantage of the tax foreclosure auction is that you will be competing with other investors for the property. 

One of the biggest hurdles right now is getting a deal.

However, the bar to be a wholesaler can be hurdled by an ant, so tread lightly and certainly don't think he has the best interest for your clients looking to sell their homes at heart. 

Some investors find success doing mainly MTR and open up some dates for STR in between contracts.

@George Bell my LLC's do two main things:1) Hide my identity, so tenants can't easily find me. 2) Separate my business and personal assets, income & expenses, not so much for tax purposes, but to avoid IRS issues.-- Just audited by IRS this summer for first time ever and had no issues!