The thing I'm getting at here is there will always be unanticipated catastrophe's that could make your investment turn out poorly. 

I've also made the acquaintance of quite a few interesting people.Fortunately, while this incident has been a significant setback, it nowhere approaches the catastrophe with which many of our fellows are faced because of the wide spread consequences of the pandemic. 

Not to mention the catastrophic lawsuit you could be facing.Please BP folks - do not give advice outside of your expertise. 

Catastrophic weather events, fire, etc. can also happen.

You can never insure enough in the event a catastrophic event happens at the property.  

Do you have some sort of strategy to be so aggressive that also prevents some sort of catastrophe down the road?

Will the real estate market suffer a catastrophic meltdown as well?

Both areas have a strong history and other than some catastrophic event there is nothing in the foreseeable future that would change that.You also seem to be wary of Vegas long term. 

I don't know if this is the case in HI or with your policy, but I have seem some insurance policies in my day that have a "waiting period" for catastrophic coverage.

The personal property (tenant's stuff) will not be covered by your policy, which is why they need to have renter's insurance for a catastrophic loss.The HOA portion:If the HOA has a rental restriction then you'll need to get their approval to rent the property.