With 5 units and some self management it sounds like this definitely isn't your first rodeo.

Even from the name that doesn't sound so good.. 

@Laura Renardo this sounds more complicated than it is I think, but yes you need a good tax professional.

This sounds more like you want the income stream than need the income stream. 

Pick any two.Great question, no easy answers.  

So with Prop 19, California made it very easy to trigger the reassessment.

Thanks,Daniel Hey Daniel,It sounds like a Refinance-Rehab.

We similarly started out with the plan to Flip a couple of houses then starting to Hold.It sounds like you're interested in utilizing methods to find off market deals which can be a great way to acquire properties at amazing prices!

@Nate McauleyIt's great that you intend to go into real estate investment, and your plan to begin with a rental, progress to house hacking, and then consider mending and flipping is a sound one.

Sounds like you're in a great financial position, especially if you're remote.