Expect to have some wall cracking and maybe even a structural issue to deal with.

I have a set system of collecting rent and a good network of professionals.

It is more about your mailer now than the actual list to get leads.Here are some tips.Most mailers, are sloppy (on purpose), doodles drawings arrows ugly text...Try to be different and be professional.

As long as your description is detailed, pictures are professional/clean, and your rental is priced fairly, you should begin to get lead calls!

Knowing that they're unbankable do I want to do what PROFESSIONALS IN MONEY LENDING, will not?

It looks like there is damage leading up to the third floor and what looks like hairline cracks in the paint that go straight down.

I’ve reached out to my mortgage broker and real estate agent who have helped me with my last two houses, but I would like to find professionals that have more experience in dealing with investors and investment properties.

You'll find a lot of working professionals in your area.

It was draining my time and funds.I just made the jump to Century 21 Professionals in Braintree. 

Cleaning would be straightforward as you would only be renting 2x year and guests would only pay for the check-out clean (unless they request midstay cleans) so maintenance would be the major key to your self-management.If your listing has not had a great response on VRBO you may need to look into hiring a professional photographer as VRBO receives alot more inquiries than Airbnb in South FL.