However, I find I usually have to do a little more education or hand-holding up-front with them (because there can be a lot of things they don't know- whether it's about how Airbnb / VRBO work or what the rental process is like). 

We paid them 9% interest (they put a private mortgage on the property) and give them 19% membership interest in the holding company LLC How did you add value to the deal?

In Florida, hold over tenants can legally be charged double rents, that is FL state law.

•Would you sell or hold, given the 3% mortgage?

You can grow quality lumber.You can cut Quality lumber.You can both Grow and Cut Quality lumber.Last you have to Sell Quality lumber.All of the above sound so basic, but until you have Failed or someone holds it in front of your face, you don't know.

So after being laid off a few times in the last 8 years I decided to get back into investing but this time focusing on buy and hold multi family real estate so that I could built wealth that could help me retire my wife who just had a long battle with cancer and survived , but is now back to work, and I want to give her a relaxing life free of all the stress of the world (by the way did I mention she is also in the mortgage lending field) so that explains the urgency to retire her from w-2 work ! 

I hear there is a potential market in the Pinole area for buy and hold long-term and even Livermore area for flipping. 

You haven't provided us with any information that would help us help you.My recommendation: do not sell a property unless you have a plan to invest it in another property that will perform better, or if selling will move you closer to your goals.If you don't have a firm plan, hold onto it until you do.

If you can hold onto these properties over time (ie cash flow sufficient to not lose money), you have already "won". 

To echo the rest of the group, if you're planning on holding the property, a DSCR is likely your best bet, assuming your investment property is in a rental area that supports the debt service.