Thus, they are more apt to be torn down since they are in central locations and larger projects can replace them.With regards to the general BP poster or reader, doubt most of us are the $100mm to $300mm investor range to consider taking advantage of these properties.Looks like you're in California. 

I recently paid someone to do my roof and replace the carpet (~5k expense) on my short term rental in 2023, however he won't fill out the 1099-NEC.

The licensed versions sold at big box stores are not the same quality and break down quickly and rarely have replacement parts.

If everyone would simply eradicate that from there vocabulary and replace it with "Realized PERFORMANCE".

If managing it yourself feels unsustainable in the long run, hiring a good property manager could give you more peace of mind.Since a 1031 exchange or like-kind replacement doesn’t seem to be a good fit for your current situation, you could consider a HELOC if you need to tap into the equity for other investments without selling the property, although rates are high so this would eat up your cash flow.

For example I had my slow teenage kids with me and I hadn’t replaced the keycard by checkout time (6 minutes past), although we were out of the property and had locked the door by that time.

I assumed some would need replaced, which would be okay, but I would hate to see it all trashed.I guess in that vein though, I hear that a lot about LTRs -- the horror stories -- and we have been blessed with amazing tenants (generally) so I was thinking it would be along the same line where it would be something where you would want to charge high-end and screen intensely to try to get a tenant that just is transitioning and can benefit from the furnishings.I know that could still happen though, even with all the precautions you can take, so it's something good to consider! 

Adding paint and replacing flooring is not going to add much value in the typical case.  

Not many people are excited to see long-time solid neighbors leave and have them replaced by a short-term rental. 

There is another argument to do the 1031 and purchase multiple replacements with cash.