@Will Fraser I’ve dabbled with the idea of focusing on a VRBO property to supplement my cash flow issue.

Even if you knew everything about nutrition, had awesome work ethic, could run 6 miles in 45 minutes and could bench 200lbs, it would be a tough sell to new clients because you don't look the part.

So I’m ok using other people’s money to help me retire with a lot of passive income to help supplement my other retirement funds.

However, I work full -time seeking a part-time job to supplement my income if you can help let me know.

In short, these are great supplement tools to make screening or receiving payment more convenient, but they are not substitutes for developed intuition and property management.

I know there's disclosures needed and time would need to be allocated to each business but I feel like the mortgage broker income would help supplement larger but more spread out paychecks from being a real estate agent while also spending my time and energy in real estate.

@Jon ReedWell said, and I agree with most of your reply on the thread - except the part about moving your holdings into bonds.Selling off a portfolio is tricky, cap gain rates are brutal, and if you are a 60 year old investor with good cash flowing rentals that supplement a retirement, why not just keep them and work to develop a tax minimization strategy, and who knows maybe you will live to be 90!

While maxing our my 401k in the first 3-4 months of a year, I’m able to supplement the w-2 income with rental’s/note business.  

They found it intriguing that, if they found themselves in employment situations without benefits, this little rental house would supplement those lost wages during times like maternity leave, for instance.By the time we finished, the kids realized that starting their adult life with a free-and-clear rental property and $25,000 to invest with was way better than what most people end with.These kids had been placed in a fantastic financial position.

I've gone to workshops/seminars at work like this, where there was a general topic (like "Nutrition") and the lecturer started off by polling the room or subject matter, and then we voted on which of those topics were of highest interest, and then the lecturer just worked down the list.As for what kids should do when they turn 18, they should get a job if they don't already have one.