What aggravates me about this situation is the HOA never communicated anything to me personally about the trash in front of the property until yesterday when I received an email of the incident and a fine and a required meeting with the board.

As a courtesy, you can consider writing him a letter informing him that beginning next month you will be enforcing your lease and spell out the section that specifics what his obligations are and I suggest that you start communicating with him via electronic mail from here on in.Prepare to file a notice to pay rent or quit as soon as it applies and proceed with an unlawful detainer.

My guess is... it's most likely something in your communications that are not helping your cause. 

I requested a refund of the unused portion only (11 months) via a ticket (since that is the ONLY way to communicate with them.  

Someone needs to take the reservations, communicate with guests, and keep the calendar updated.

This is very surprising to me that an email to them went unanswered - please forward you communication to [email protected] to me ([email protected]) so that we can get to the bottom of this. 

start fully documenting everything and take lots of pictures, I would start communicating via email or by letter, even send them a certified letter stating damages etc, sounds like you didn't hire a qualified roofer. send a copy of everything to your attorney maybe even have him draft a letter demanding a response, if push for a refund + damages and go with a new roofer

We will be making an effort to develop our website more so that applicants can see what we're looking for and help streamline the communications back and forth, but this is the first time that that need has become apparent.Thank you for your input and advice.

This prevents us from working with fly by the night clients as well as wasting our time and preventing any miss communication.2.

@Andrew MerewitzState of LLC FormationIt is normally advised to create the LLC in the state that you will be holding the real estate; Florida in this case.If you created the LLC in New York - you would be required to register the LLC in Florida; increasing your total costs.Please also be advised that it can be costly to form an LLC in New York.Location of CPAThe important aspect of looking for a CPA is that he/she understands the taxation of real estate.Technology(emails, phones, skype) allows you to communicate properly through an accountant eventhough he/she may not be in the same city as you.Florida does not have a state income tax.