Maybe being a limited partner with some of the really good syndicators out there is an option to this route. 

@Robert Brock, I guess my advice is not really any different than I would say to someone wanting to be a residential wholesaler: you need to add value to the transaction.Often times, having the deal tied up is the value, but more often then not, in my limited experience with commercial wholesalers and residential, the wholesaler has no idea what someone will actually pay, so they tie up a deal at too high a price and then add their fee that turns a bad investment into a horrible investment. 

If you can't even criticize those that are not, it says something about YOU not me...."

Rehab: Adding Value Through RenovationsThe rehabilitation phase is critical.

Penalties of these Federal charges may include:30 years in prisonUp to $1 million in finesThey have a "statute of limitations" - (with a third "T"  ;-) of 10 years from the date of the transaction - 10 years from now, you could get a very nasty call and hopefully, you put your reserve money in a good account that grew to cover legal expenses**********************************************And the universe could blow up as Doc says in Back to the Future " But, granted, that's the worse case scenario." 

Minimum of 3 night stays, limited number of STRs in a particular neighborhood etc.You need to get the license and pay the STR tax.

I understand there are many limitations to short-term, or even mid-term rentals down there now, but hoping to see some insights on areas where I might see more of a demand. 

Since I have limited cash to deploy, I do not want to waste it on iffy deals.  

Once you move to Chicago, look for similar groups—Chicago has a vibrant real estate community.Building a Team: Since you’re new, connecting with a knowledgeable real estate agent, lender, and property manager in your target area is critical.

Can I use my current homeowner policy and just increase the limits?