If it was up to me, the regulation would be very landlord/owner friendly, allowing the owner of a property to lease it however they want (long term, furnished, unfurnished, short term, etc.) as long as they comply with housing rules and establishing punishing mechanisms to the tenant (when doing something against their lease terms) and AirBnb or any other similar platform (when either they do not follow the proper steps to ensure the property is listed by an authorized person or when notified by an owner, they don't take the listing down). 

Sid,The way to do this is not starting with the mechanics of real estate investing, but the motivations of why you want to do it.

Bring a contractor/roofer/foundation guy with you if you are serious about the house and serious about giving him repair work until you learn these things.Key things to look at when buying a house is the roof/foundation/sewer/mechanicals/framing specially on older homes.  

I am trying to better understand the mechanics.  

Clarifications on how best to track and deduct interest using a HELOC under the new rules would be extremely helpful both as we move forward and as we beef up documentation for the past year on those amounts that are not paid off moving into 2018.One of our main funding mechanisms is a HELOC on our primary residence. 

It is mechanical so requires a manual code change.

Nik,If every unit has an isolated water supply - even if they are T'd from a main (3/4" - 1") trunk line on each floor -  then sub-metering is fairly straightforward - make a straight run from the manifold {you will build} in the mechanical room/basement to each unit.  

You can have a mechanic inspect the car for you and cars these days are built pretty good.

Over the summer i saw a building in DE built in 1682.Typically older buildings do not have up dated mechanicals, electrical, heat, plumbing and AC.

Especially when I talk to numerous realtor who are clues as to the basic mechanics of insurance when it comes to their own home insurance.