That's not what I'm asking about.A year later, on 12/16/2016, at the original maturity date of the loan, the maturity date was extended another year and a new document, entitled "ASSIGNMENT OF LEASES AND RENTS," was signed by both parties.

The reason why I like this strategy is:- Seems like lower risk;- If numbers are correct, its not much out of pocket;- Seems like a good way to get feet wet, get a rental & some positive cash flow.My concern is:- I speak with investors all the time who started off in SFH and they all say moving forward their strategy will be multi family.Any insight is greatly appreciated!

I suggest you speak to your CPA or hire one to make your employ good business practices at the beginning of your real estate career. 

Ask to speak with some of their current owners and current/former tenants.

Have them speak with your partners  (= family members) directly.

Everything I read online speaks of requiring the certification/exemption at lease turnover. 

Technically speaking this would be my secondary and I would be in it for a very short time (month to month and a half), but I do not want to go through the entire process only to have it fall through.

I pretty much came to this conclusion after making the thread but now I'm much more confident this is the way to go - I'll suggest they keep the house and take out a home equity line of credit while I act as a the project manager so to speak for a cut.It's good no one will pay capital gains tax, but what kind of tax can I anticipate for either of us in the state of TN (even a rough estimate would be helpful)?

I am speaking general here.

,You will want to speak with Ken Davidson BP doesn't like me posting phone numbers so I'll send you a PM.