Enjoy the ride.

He  painted a picture of them riding in and saving the day..

Would you sell it or let it ride?

Some carriers offer loss assessment insurance, which can come into play when the HOA experiences a large covered insurance loss, such as a hail storm requiring roof replacement or a fire requiring building replacement.  

This would mean your class of tenant causes more damage than expected, or hail destroys your roof *every 5 years* or something similar.

If he did not have the funds to ride out those difficult years, his investors wouldn't see their money back.

To save money, management raised the wind and hail insurance deductible from 5 to 10 percent.

I would go with a hail resistant 30 shingle then you get a discount from the insurance company .

After years in the highly active BRRRR, sales, and rehab realms as an RE broker, I quite enjoy throwing on my boots and riding a zero turn mower, taking a Jon Boat out on our pond, or cutting up a downed tree for firewood. 

That's like saying nobody got paid to give rides until Uber.