For educational purposes and future planning, is there a downside to having a large net operating loss carrying over into future years?

You have to have someone fill in the gaps for you.You can do this on your own, don't get me wrong, but the time loss and the costly mistakes don't make that approach worth it, in my experience.

You aren't going to take someone to small claims court for damaged paint or anything, and if a major loss occurs the tenants are almost never collectable anyways. 

We started at 80k in car debt at the beginning of the year, re-evaluated, took a loss by selling one of the vehicles and paid down another.

Thank you,  This is not normal (in fact this is crazy talk) and you should be dumping this contractor, perhaps suing him to recover some of what you've paid, and getting a new contractor.

Although insurance may cover the rebuilding of your property, it could be vacant for months or years until the community recovers and people return.Operating costs: Every dollar lost to property taxes, and insurance is a dollar less for you to live on.Rent control: Government control of your rental property can transform a promising investment into a nightmare.Location Selection Process and ToolsYou can try to analyze all possible cities in the US and select the “best”.

(But it wasn't apples to apples.)I looked at AirDNA's data recently and don't disagree with their broad picture but again, people here know that the details and other factors can tell a different story and bring success for some in the same area (comparables) and loss for others.I'm all about reducing risk and my read on climate data and global economies (& yes, politics) incline me toward continued investment in properties that have multiple channels of revenue, above a certain latitude, and more upscale.

I would just cut my losses and move on.

With the cause of the loss probably being a hurricane I would make sure your hurricane/wind deductible isn't insanely high though as sometimes it is a percent of whatever the home coverage is.

Hopefully your insurance policy also compensates you for loss of use - where it continues to provide you your rental income.