Understand the following.

From my understanding from some friends in Florida that are in the business , finding houses to flip and make decent money is difficult , and they are established in Florida . 

Leave it.You should understand the long term cost/benefit of every improvement you make in an LTR.

Understanding one another's difficulties can lead to better solutions.Make sure that any modifications to the rent payment schedule are noted in writing, perhaps as an addition to the lease agreement.

I have spent around $500 this week, and I do understand sometimes like this things do happen, but if this does continue and something seems off, do you recommend I tell the property management to conduct another inspection or to change the lease terms where the tenant pays for any small maintenance fees.

If you come across this situation make sure to talk to local attorney so that you understand your responsibilities in your location.

You don't need to know everything to get started; you need a foundation to build on and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.

From what I understand, you can deduct the entire premium as it is an expense to run the rental property.

Can you recommend someone in Tampa that is more broad in their experience then a traditional lender.I want to make sure I understand what you are looking to do.

Something I don't understand is the peak season.