As such, I would argue that the founder's experiences are of less importance for investments being considered today versus 4 years ago when the founders were seemingly still running day to day operations.

@Troy GandeeYou make a great point, and this sometimes is where people get stuck - in many instances people rely on their interpretation or opinion of things - but In reality if you are the only person or minority who holds that opinion and everyone you need to do business with has a different opinion - you can argue till your blue in the face but if everyone around you who you need to close a transaction will not do it, does it matter what your opinion is?

Now: Pay contractors what they're asking.Then: Argue with tenants about what to fix and what not to fix.Now: Fix everything. 

And arguing on a "what-if" scenario that is wildly unrealistic. 

Less of an issue with a duplex.Lastly one might argue that your tenants will stay longer in a SFH vs a duplex.  

Therefor I don't want to hear anyone argue  they simply don't have those relationships as an excuse. 

Depending on what one can defensibly argue for the allocation of the sale price, it may or may not be an issue. 

And these that I mention above are the very basic ABC's of it, super basic stuff.

And you could easily argue real estate has better tax advantages than an IRA. 

Some may argue it’s not necessary at the start, but it becomes costlier to transfer a property held in your name to an LLC at a later time and this is good forward thinking business planning.Don’t worry about forming an LLC until you execute an agreement to purchase real estate.