@Jimmy LieuThanks for your response , would love to connect as well please provide me with your recommended referrals .

Check out some CRM's that provide you with a phone number to use. 

Even though this moisture didn't come up through the floor, it can also provide a place for mold to grow.

Thanks everyone  You will want to speak to an attorney familiar with securities laws as it appears you are providing financial advise and would need to get some type of FINRA license 

It will provide everything you will need for managing rentals in a much more thorough way than I could write out here in the forums!

For example, Would they entertain owning two houses, if the FL one supported itself and even paid for their new primary residence, if it brought them income and they never had to spend a second thinking about it?

I can refer someone who will certainly at least answer some of these questions for you and possibly provide solutions.

I'd love to hop on a call sometime and see if I can provide any helpful input.

If not, it may be worth it to pay them a small fee to walk through the property with you and provide their guidance/expertise.

I know you will find a ton of encouraging and helpful people here.Regarding HELOC I suggest you connect with my good friend @Michael Barbari...I believe they can still do up to 90% which is 10% more than most banks.If you need any other specific connections here in Chicago I am happy to provide them.