In my opinion, making an offer site unseen is not a risk.

Do not offer to pay more rent ever to make the deal happen.   

I know I could have a family member co-sign a mortgage with me but not sure the best way to approach that conversation and what incentives I’d be able to offer to make it worth while for them other then their “familial duties” haha. 

I second @Erik Estrada Chase offers great programs for business, multifamily, and conventional loans for commercial properties.

Steadily does not offer insurance in Florida

They look to have some success with taking deals full-cycle and currently have a sun belt multi-property offering that I'm researching.

The city offers a mix of high appreciation potential in certain areas and solid cash flow in others.

In my limited experience with a similar service, they will send you leads and even make offers but you still need to do your due diligence and make sure it's a profitable deal for you.

Explore Financing OptionsChicago offers excellent financing opportunities for house hackers.

Companies normally offer limits up to$500,000 but some offer $1,000,000.