That being said, it is almost universally believed that to arrive at a cash flow number one “modifies” the profit and loss statement by adding back not cash expenses such as depreciation.BUT, here’s my issue.  

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.

No way I would put fancy shades in any STR.

Consider it a loss and tell them they have to move or you will start the eviction process.

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

What’s your “loss”?

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.

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

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. 

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