I'm sorry for your loss.

That's the cheapest I can get with replacement cost and a $5,000 deductible, no loss of rent coverage, etc.On a quad, I'd expect you're paying at least $250/mo or more.Lawn and snow removal also seems quite low.

Is it even worth considering renting at a potential loss of HOA, also knowing home repairs could be needed in the future?

Not many companies off comprehensive STR insurance but there's a few, and you may get extra coverage on loss of rental income, bedbugs, etc.

The first rule of gambling is that no single loss can wipe you out.

My rule number one is- don't have losses. 

What’s your “loss”?

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.