Given the nature of the lot --  around 100' of frontage, ~ 250' of depth, with the existing structure more or less centered at the frontage, I believe the existing structure would need to be torn down to subdivide.

@Aaron White over time it will become second nature.

Two minutes walk to the trail of 350 acre park and nature preserve and .40 acres (ok, I admit it, I actually purchased the property for my Australian cattle dog . . .)Purchase price = $342,500.

@Kyle DeSimone so much is going to depend on the tax nature of the profit sharing plan. 

. -- I see why he wants to avoid paying $3,500 - $4,500/year in natural gas, however, now we are stuck with overpriced units and in area where renters expect heat to be included. -- He can at least remove the radiators and cap the pipes to provide more room in these 2 bedroom apartments.I'm all about new windows, updated kitchens/baths, etc but I think he went over the top with these new HVAC systems..

Wealth is created from de-leveraging real estate (your tenants paying off your loans) and from appreciation, both forced (remodel) and natural (hopefully).Adding a single property now to your portfolio will set you a world apart at your retirement, when it is paid in full and you still own a cashflowing asset.

If it’s flooding from natural disaster, there’s no recourse per say.

Nature stone 

There are both good and bad new.Unfortunately, if you are living in the property, it’s a personal asset and all the expenses are personal In nature. 

If it states that any home appliances repairing shall be borned by tenants.Otherwise, naturally it will come back to the landlords.But like what @Jane S. mentioned, you basically got back the ROI.