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.  

I have two beachfront condos and im looking to supplement my current insurance with better hurricane insurance and add flood insurance. 

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

Each property is different, so it is natural that the terms may need to be tailored specific to a property.

Therefore, any losses from the apartment complex would be passive in nature and would not be able to offset W-2 income -- they can only offset passive income.

Do I pay that down faster or do I save for my next down payment and let that debt drop off naturally.

I happen to enjoy my W-2 job, so my goal has been to supplement that with cash flowing properties that will provide additional income now and in retirement when they are (hopefully) paid off. 

Solid wide oak floor that we refinished & all the built-in natural wood cabinetry had leaded glass doors as were the windows. 

Account Closed starting on the exterior / rebranding first is a good approach, as you want to give he apartment a newer, more upscale image.You should naturally weed out the less-than-desirables as you implement your rental increase, this is also where you'll have vacancy opportunities to renovate units.