However, I feel like there was an opportunity presented in stocks the last few months so I am taking advantage of it.  

That's what investors say who don't know how to use the MLS to their advantage.

My idea is to sell my house to the LLC biz (which I realize is a sole-proprietorship to the IRS), and take advantage of the Home Sale Exemption for those capital gains.

We do have the advantage of being a high demand city.As for turnover costs, we classify that as maintenance/cap ex.   

Originally posted by @Scott Wolf:@Hai Loc I know Cuomo issued a moratorium on evictions that lasts until August 20th.https://ny.curbed.com/2020/3/26/21192343/coronavirus-new-york-eviction-moratorium-covid-19Thanks for infothis particular tenant is still working and is simple milking the system right now.. all my other tenants are paying even the ones who got laid off.. he is a one off that is taking advantage.. even if this guy catches up I will evict him when the time comes 

This would create some additional capital for our LLC with having a guaranteed buyer, eliminate realtor fees, holding costs, etc, but we would also be able to take advantage of individual mortgage terms - 30 year amortization, 3.5%, for instance, with a separate bank that we have little exposure. 

I also feel due to my position and life experience this is an area I have a relative competitive advantage in so I want to start here.I live in China, speak fluent Chinese, as well as having a Chinese Fiancee and a large network of wealthy investors hoping to get some money out of China to diversify and potentially provide opportunities for future Children.

@James E.Seems like you are doing the work of your CPA...I hope you are getting a discount on his services by doing your own research.In short - there are time limits of being able to take advantage of section 121 exclusion...however there are exceptions to the time limits in which case you may be able to claim partial exclusion.Your situation is unique since you and your wife both appear to have separate houses that qualified for section 121.

The advantage is that you have the flexibility to lower your payments if something unexpected comes along.

Should I take advantage of the no penalty for pulling money out of my 401k?