Even if a family has high coverage, the insurance adjusters still want the lowest option so it's important to also be competitive. 

Also, you have a lot of competition with Disney and Universal properties.I always stay at a Disney property to take advantage of the included transportation to easily park hop and not deal with having to drive and park.

Depends on really what you are looking for:-Speed - some HMLS can go "no appraisal" so can close very quickly and beat cash offers if you are in a competitive market to buy-Interest Rates - can range anywhere from around 8% to 13% (same with "points") but not usually as huge of a concern for flippers since the terms are so short-Leverage - depending on your risk appetite / capital - this is also a top concern for some (almost always over and above rates/fees) can see anywhere from around 80% LTC to even mid 90s LTC (including 100% of rehab budget)

Research competition  and determine their profitability and how much they spend on marketing, how many employees they need, and how much time the wholesaler needs to devote to the business.  

For doing an STR well the larger properties are best and it needs to stand out amongst competition to perform well. 

Then you have a competitive advantage.

After identifying the property’s potential, we negotiated a competitive purchase price of $28,000 by highlighting its renovation needs.

I find myself spending a little more off season than on as I do more tweaking and research to remain competitive and in front of eyeballs.  

This would be primarily due to your competitive advantage of living in Chicago and knowing the market.

The Smokies are a favorite of mine, but beware it is an ultra competitive market.