Wind is one of the subtle items that Insurance companies are starting to exclude. 

An assistant can do most everything that you need done and they work directly for you rather than a property management company that has several clients and you’re just one of them.Also, again, depending on the location of your properties, have you considered doing a lease with the option to buy?  

Essentially, your new replacement property will consist of (1) a thirty plus year ground lease on the real property you already own; and (2) new capital improvements made on the real property you already own pursuant to the new thirty plus year ground lease.

One long-shot option is to offer a lease at something like $1,300. 

This is not the utility company's responsibility.Your lease should state the tenant is responsible for maintaining utilities.

Due to item 1, adding an ADU can require years to start achieving any return (once the accumulated cash flow recovers the initial negative position).4) Adding an ADU is a slow process.

The other business I run is reselling, listing items on eBay & FB.

By making partial dispositions, you can also avoid subsequent recapture on these items when you go to sell.

This is true for bonus depreciation items as well.  

If you feel confident in the tenants signing those long term leases, this is a slam dunk and you'll have a cash cow on your hands very quickly!