Passively investing in passive income generation

[Kevin McGuire]

Hello fellow BP'ers,

I have a friend who is starting his retirement but is anxious about no longer "getting a paycheck". The issue is psychological, not financial. He's been financially fortunate working in high tech, is frugal, and logically knows he'll be fine financially. However, as I understand, it's normal for one who has worked hard and saved, seeing that savings number go up all the time, to freak out at the idea of seeing it go down, forever. For my part, that's why I got into real estate investing, for the financial and psychological comfort of passive income generation without depleting your capital, but he doesn't have the inclination to be a landlord. He would qualify as an accredited investor.

I'm encouraging him to look at passive income generation outside of stocks and bonds. I mentioned to him two alternatives:
A) Hard money lending

B)  Investing in a real estate syndication

Questions to you helpful folks:

1) Do you have other avenues you'd suggest?

2) Regarding syndication, are there posts, sites, or books you could point me to that I could pass on to him? I only have passing knowledge and have wanted to learn more anyway.

Thanks in advance,
Kevin

PS. Honestly, it really is a friend of mine, it's not me asking like, "I have a friend who has this embarrassing rash..."