I would agree with @Steve Vaughan I kind of straddle the fence since I am an active investor and also own a property management company.

I'm in the mid-Atlantic, and the majority of the homes here are not new construction, so I think ours kind of straddle the line between A and B properties.

Some straddle the parcels and had one address.

Holding a property more than one year straddles two tax years.  

It can be hard to straddle the line sometimes, but I've been burned by other tenants as well (painting, extra roomies with paid utilities, spraying cats) so in my opinion if its a fairly easy place to rent, why stress over someone who is already causing you angst?

Just out of curiosity, you really straddled the country with your properties, were you military at one point?

Before you do anything.. go sit down with a local land planner engineer and have them tell you what you really have.Also go to the county planning and see if your shadow plat can be reverted to legal buildable lots.in Portland this is quite common its called a lot confirmation.A little history on the West coast.Our cities basically expanded from San Francisco back in the 1800's and the same engineering firms that platted SF in the middle 1800s also did Portland and many other cities.. so they did this with 25/100 lots on a grid pattern.. its those 25 X 100 lots that are under your plats and sometimes 50x100  unless someone did a reversion to acreage or combined them legally many times they are still legal lots.and or like Portalnd they have all sorts of funky ways you can resplit them easily.for instance I have one right now  were I had one home it was a tear down tore it down. it had 4  25x 100s  but because the house straddled the middle two they would only allow 3 lots.well I confirmed 3 lots then did lot line adjustments so I got 1 skinny  28 and 2 36's  the 36s I sold for 50k premium over the 28s and a 50 foot with two 25s  would not have netted me as much either .and to be frank..

I straddle the 'paper' and RE universes and are very pro for both.

As it straddles the TN/KY border both states have a very significant economic interest in seeing it remain open. 

@Colin MurphyWelcome to BP.While it is probably premature to create a holding company for your future properties at this point, it is good you are thinking about it now.A Limited Liability Corporation (LLC) is an entity which straddles the worlds of sole proprietorship and the corporation.