But it might make sense to work with folks who can offer more focused guidance on filling the knowledge gap you have.If you shoot me a DM, I can also ask around for more of 1:1 coaching opportunities. 

However, our research indicates that many DSCR lenders require Florida properties to be held in an entity.Are there any DSCR lenders that offer loans for properties held in a personal name?

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. 

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

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

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

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.

Steadily does not offer insurance in Florida

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

Explore Financing OptionsChicago offers excellent financing opportunities for house hackers.