I also make a pretty nice living with my W-2 job, but dont feel fulfilled working for shareholders and ungrateful clients. 

My daughter is a 2% shareholder in X LLC, which greatly reduces my audit risk. 

However, if any of the employees are greater than 2% shareholders, the health insurance premiums are included on their W-2 as compensation. 

It gets more complex because when the purchased occurred I was a 50% shareholder... about 5 years ago I bought 1 partner out 30% so was an 80% shareholder.  

I also get tired of having to explain that by "making a relationship" with you, I expose myself to litigation if I ever have to sue a borrower for a deficiency from a foreclosure and oh, let's not even mention the part about how I have to explain to my state and federal regulators, or my shareholders that I failed in my duties to maximize recovery and minimize risk of loss by selling directly to some invidivual investor instead of exposing the property to the open market....you keep digging.

@Cole MitchellYou can certainly sell an asset by an S-corp to the shareholders as long as the sale is at an arms length transactions.The questions is should you.If you plan to acquire it in an S-corp(you will be forgoing the section 121 exclusion which you said you are okay with) if you are going to just sell it within a year - you should just sell it directly from the S-corp.Transferring the property from the S-corp to you personally and then eventually the buyers will cost more in title work.

Zillow will probably follow the same strategy since they have to think in terms of high quantities to make share holders any money.

My concern is that what if the existing shareholders don't want to sell the shares, then, will they become a partner in the deal or just continue owning the shares equivalent to the apt sq ?

They don't want to do the work and would rather buy a stabilized asset (like the portfolio of apartments I worked for) and just reap a nice stable return for their shareholders. 

My concern is that what if the existing shareholders don't want to sell the shares, then, will they become a partner in the deal or just continue owning the shares equivalent to the apt sq ?