That means there is not really an effect on the debt to income ratio neither positive (income) or negative (loss) but rather simply making that payment  non issue. 

The only issue is of course it will be expensive to bring a photographer 3-4 times!

None of these communities will be changing to residential neighborhoods, although a couple do have residential 'sides' that full time residents live in and can not be rented short term.Two of the big communities that you will have some issues with self managing are Reunion and Margaritaville.

Quote from @Jim Stanley: You should reserve insurance for large claims.Contact the city and report the issue to them.

The HOA can decide to do a special project or make a short 3 story elevator more hurricane proof ($800000) or have issues after a hurricane and then you are definitely not ahead of the game.Please connect with me and I can maybe point you in a better direction.

Having the tenant be responsible for something like the first $1000 of each maintenance issue, or $500 can be a big help.

They may also be able to temporarily relocate your tenant to avoid any other issues.

My underwriting would have this large negative cash flow for 7 years.I would do a thorough underwriting but want to show using quick math the issue so I will use the 50% rule.  

I don't see it as an issue but many still do, at least in my small town where the majority of renters are elderly people looking for low maintenance housing options.

The buyers did a long inspection, multiple days... made a huge request for concessions based on what we knew to be purely made-up issues.