There are many ways to buy cheap elsewhere but still lose your shirt. 

@Phillip Austin someone who obviously should not rent but buy themselves a brand new house. what was their previous place?  

The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon). 

I work with agents who know my buying criteria, and they bring deals to me before they hit the public market.

If you plan on buying additional property, you should indeed go on more calls to assess and meet the repair person so that you understand the problems as they arise.  

If you were looking to buy a fixer upper etc..

It’s clear that there’s an incredible wealth of knowledge and experience here, and I’m excited to continue learning and growing with this community.I’m looking to connect with members who are open to mentoring or collaborating on real estate deals, particularly in buy-and-hold strategies for single-family or multi-family properties.

So, they could potentially buy another house later on.

My previous renters were relocations - either had sold their home and looking to buy another (low inventory so takes a while to find a home to buy) or moving here from another city and didn't know yet what neighborhood they want to be in, or alse building a home and need a place to live until it's completed.

Given that I'm not positioned to buy just yet, and simply running the numbers, is there a rule of thumb for estimating insurance costs that would make sense in Cook County?