Since you're looking to expand into Florida and other states, I'd recommend starting by narrowing down your focus:Market Research – Florida has great opportunities, but each state and city has different laws, taxes, and demand drivers.

Does anyone have any recommendations for a property manager or insurance broker?

Investing in Wisconsin and Illinois is a great move—both states offer solid opportunities for multifamily and single-family rentals.If you’re looking to connect with like-minded investors or agents, I’d recommend joining local real estate meetups or REIA groups in the areas you’re targeting.

I'd recommend reading these articles on BP for answers to all your questions!

I would recommend fixing it and then determining whether or not to sell based on cash flow and profit after the sale.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

If not, I do not recommend sheriff sales as a first attempt.

I am in Brent Daniels' TTP Mentorship (which is excellent - HUGE value) and he recommends Batchleads (but not their dialer - for that he prefers Mojo) and I think I should just stick to what he said, but I have serious "shiny object syndrome" - my bad ;)!  

Most professionals will recommend a separate LLC for every $1 million in assets, but I don't think that's necessary.

For newbies, I recommend starting with a turnkey cash flow rental.