Made a very nice profit complete with the added RE note annuity.

I HATE annuities.

One would have to describe why it's safer than a CD, Bond, Annuity (which is federally insured) or just the S&P 500.

I would consider this option only if I were truly at the end of my investing life and seeking to create an annuity-like income stream through a simpler and more consistent vehicle, saying putting it all in IVV and withdrawing a flat percentage every month. 

Beside the use of a single asset entity as noted above, the basics available to all are that your retirement funds are exempt from creditor attachment either through Federal or state law; annuities and insurance is exempt in Texas, Florida and a number of other states, as well as homestead exemptions.

Would like to roll a small annuity I have from a short lived stint in a union into a solo 401k.   

The management business is asset-light and operates almost as an annuity business because of long-term management services contracts. 

Income Flow: Is it feasible to have the rental income flow to the family member, akin to purchasing an annuity, thus providing them with a steady income stream?

(I share Chris's view that the energy sector looks good and may outperform RE.)I'd advise caution when someone suggests you use the balance to buy cash-value life insurance or an annuity.

IMO better options- If you don't need the money in the next 10+ years look into Annuities I'm seeing 7-9% and you don't have to participate in market downturns.