Currently renting both apartments for a average monthly cash flow of $1000 Lessons learned?

CASH Lessons learned?

another property to the portfolio, and a continued relationship with a live long client Lessons learned?

There comes a point where having a real estate-savvy tax preparer outweighs your time learning a new software. 

It sounds like REsimpli has a lot of value and combines a lot of features so I don’t need to pay for subscriptions to 10 different platforms (and invest a ton of time learning their systems only to discover a better option and start the process over again).

Learn how to source motivated sellers and negotiate win-win deals.

Learned a lot and came out with $14,000 in my pocket Lessons learned?

Between now and then, I am committed to learn and connect as much as possible!

Definitely don't sell it and buy cheap Class C in Texas or other state for "cash flow on paper" - I learned a painful lesson with those types of properties. 

Flipping homes in San Diego has been an incredible journey, and over the years, we’ve learned a lot about what works—and what doesn’t—in this market.