We are still in the early phases of planning the transition.

I am going to house hack (live in one unit of the property while renting out the other one or two units).My question is this: how do I transition from house hacking a duplex/triplex to having a real house of my own and also expanding my RE portfolio?

It's a little more than I would ever need but if you are a wholesaler or somebody that want to do more targeting mass marketing it looks pretty great.   

Will be transitioning to living in CDA full time in a few years.  

Banks like to see you showing income but we have multiple businesses that run with little profit and yet are able to live without being forced back into the W-2 world.I forget what book it is that talks about the masses working from January until May just to pay taxes on their income.

How long with that transition take?

These tenants are use to one way of leadership and it is hard to make a transition.

Thoughts from the masses?   

We do have some rental properties as a safety net during the transition, and I'm not sure I'd have the nerve to leave a corporate job to become an agent without some passive income, substantial savings, or a working spouse to cover the transition.I think everywhere is probably saturated with agents, as is typical during a real estate bull market. 

It also means being an accessible resource with a strong local network of moving companies, handymen, cleaning services, gardeners - or any similar service that may be required to maximize the listing and provide a smooth transition for the sellers.Finally, selling a home can be very stressful, and a good listing agent should be a master of managing their sellers emotions and expectations.