You need someone local or a management company that is equipped to handle the management of these properties.

The in ground pool that was so gorgeous in the pictures was trashed with a ripped liner and no equipment.  

Hi John,Have you thought about 2 separate systems made up of non-fancy basic equipment.2 Basic furnaces,  2 basic A/C's, 2 basic thermostats.Also have you thought about separate electric meters, water meters (and water heaters) and gas meters--that's a nice setup.Does your zoning allow this (meaning is it zoned for a duplex or are you (flying under the radar))Because pulling permits for non-zoned stuff (???)

Exercise equipment, or at least boxing gloves and headgear. 

We have tons of flip ready flooded homes from 2011 that many are too hesitant to buy or fix up because it's the second time the area has been flooded (first time in 60s, and City has bought out with new plans and prevention, but buyers still weary of mold/foundations etc)It's a very option versatile house/market, i would love to rent it but hard cash and we're Young with current mortgage on our home with HE credit lines out this last year or so to get our Corp and everything setup and our subscriptions/dues etc for our accountant/attorney packages,education, marketing, and expanding our tools/equipment for the contractor work we do ourselves.

Historically I have filed Schedule C with my major expenses being in travel (combination of mileage as well as airfare/hotel for related conferences) and depreciation (equipment).

It seems nice to loan a chainsaw but basically it  is not equipment I would take a risk on in case they get hurt. 

The pumps and electrical equipment have all been replaced.The other concern for me is the septic systems.

.), electric vehicle supply equipment (EVSE) costs (physical charger hardware, etc.), equipment for usage monitoring/billing, permits, etc.

Beautiful piece of equipment, but it is long overdue for a flush out.