I think the HOA is trying to protect from something they don't understand, I want to work within the parameters of the HOA but with a different mindset than anyone else has used. 

Quote from @Alecia Loveless: Always protect your Property, Time, Income, and Sanity (PITS).

Wealth is for protection from unforseen events and emergencies.

Do not just get randoms, this is going to take a lot of work to protect your privacy and personal residence.

A well written management contract should clearly spell out what is expected of both the PMC and the owner, to PROTECT both and avoid misunderstandings.

LLCs are mostly for legal protection, and this protection is hotly debated. 

I too offered agents the ability to offer the renovations without any upfront cost to the sellers and we would get paid at closing, of course this requires some documentation that stipulates that can not back out of the listing and other protections since we would have our money tied up into their home.

Be sure your attorney drafts the documents for your protection . 

Each carrier will evaluate the property and determine what the cost will be and that's why each carrier has a different premium for the property with generally 85-90% of the coverages being the same.If you feel the dwelling is low see if they have a guaranteed home replacement endorsement that can be added or 150-200% dwelling coverage to truly protect yourself in the event of a total loss.The market is going to be like this until 2025 most likely so the easiest thing to do is raise your deductible without sacrificing coverage.

Also, check to see if the utilities are current and if they are breaking other terms of the rental agreement to protect your interests and shore up your case.