Part of what keeps the area great is everyone is terrified of "Detroit" and labels the entire area as a "war zone" whereas, we have markets of entirely $500k homes.

These are some of the ingredients you need, to move forward.I would suggest you join a local REIA club in your area.

I think the more likely scenario is that they labeled the work order wrong when uploading it.

Seems like the categories on airbnb and/or vrbo are restrictive in terms of labels, so I am not sure how this could be done. 

I am pretty sure an insurance adjuster would label this normal wear and tear.

I KNOW a lot of you are going to be like “well that’s a very broad category”😆 I get what I’m trying to say is that, my mind is kind lost on how to structure what deductions under which label (very general) but what if it was for an “unusual” purchase.

On the google email optimization I also use labels and Boomerang. 

Assuming what I paid is considered "Fair Market Value" (the Market Value labeled in the property appraisers office for 2021 is $166,080): $200K x $150K/$200K = $150K which means I would not realize a capital gains.2.

Found out after the fact that having a registered agent in Tennessee & registering LLC in Tennessee is the way to go to avoid being labeled as foreign entity for taxes

It was a lesson learned, from now on everyone will book through the apps so that the dates are automatically reserved and appropriately labeled!