I work with larger properties all along the gulf coast. The kicker on hurricane damage, or any 'named storm' is the deductible is a percentage of the property value, not the damage. A couple of years ago, I negotiated a $2.7 million claim, with a $1 million deductible. Even so, the property in the end benefited from the renovation. All hurricanes do not devastate the entire area, and they are few and far between.
The management company I am with, deal with lots of low income deals. If you go with Section 8, my advice is don't put up with the riff-raff, enforce your rules, and evict disorderly or destructive tenants. Make your property desirable.
Advertise on Craigslist several times per week. The applicants will come. One of the biggest problems in the industry is keeping the vacants ready to lease. The applicant gets a voucher and can choose where they use it. Good management can usually stabilize a property, if you aren't in a war zone. With Section 8, you will have to jump through a few more hoops, to make sure you comply with certain standards. They have pet-peeves about where smoke detectors are located and such. They will inspect the unit; give you a list of items to repair; re-inspect. On the initial inspection, if you fail 3 times for the same item you will lose the prospective tenant. If its on an occupied unit and you fail the 2nd inspection, they abate rent. If you pass on the 3rd inspection you can recover abated rent. Fail the 3rd inspection you lose abated rent and the voucher. You will be responsible for pest control even if the tenant doesn't keep food put away. Just some examples to prepare you for the housing authority. The positive is you receive payment from the housing authority, not the tenant.