At the time of purchase, I knew I might not want to stay indefinitely and at some point to might convert the home to a rental property.

Do Florida rentals still pencil out with current insurance rates?

These are 668 square feet and will rent $1600-$1800 depending on the urban adjacent neighborhood. that's rental prices of $2.39 to $2.69 per square foot. that's on a long term rental. on a short term rental the prices would be higher but we haven't had any clients do that yet.

Verifying last 2 years of rental history very important!

Avery Carl's Book, 'Short-term rental, long-term wealth' How did you find this deal and how did you negotiate it?

For example, before he switches a policy from short term rental to long term rental he wants pictures.Is it normal?

Spoke with multiple credit unions and they mentioned a rental property needs to show at least two years of rental income in order for that income to be counted into the DTI ratio. 

With that said, I am in the position where I will not need a monthly income from my rentals.

I have REPS by actively and materially participating in my rental property portfolio, and also work as a real estate broker full time (1099 collecting commissions through a single member/purpose LLC) from buildings I sell.My losses from my rental properties (LLC #A) largely offset any federal and state taxes from my brokerage business (LLC #B).

Would you consider trying to self manage rentals in my situation?