So, naturally, I came here to see if any of you lovely and experienced people can lend a recommendation for a vetted and experienced property manager.

Appreciation The natural rise in value real estate tends to experience.

I'm naturally an optimist, but I really do believe that the number of landlords that treat their tenants like they are just numbers on a spreadsheet is much less than people who treat them like humans.

My personality and nature is actually wired to be loyal, but almost to a fault.  

In reality that is just the nature of the beast.

Another option, since it looks like you have less than 4 financed properties, including subject you could also do a renovation loan on the property, that would allow you to incorporate the renovation costs into your loan and you would just have to come up with the down payment. 

This is so true and I enjoyed reading this CJ.Everything of this nature takes time, patience and lots of learning!!

However, my question is about damage that occurred because of natural events, made worse from neglect.

Having multiple properties minimizes downside risk of vacancy, natural disasters, and you don't have all your equity sitting in one place, which is a target for lawsuits.  

It's all a 1231 loss (which is ordinary in nature).E.g.