I provide some coaching and mentoring but mostly for people who have a job or own their own business but want to invest on the side for supplemental income.

My thoughts on this are that you are going to live SOMEWHERE anyway, and you will probably pay SOMETHING anyway - so why not get tenants to supplement that.

Another option is to add supplemental financing to a deal once stabilized and keep the original financing in place. 

Long term I want to be investing in commercial real estate with a focus on multifamily properties to build up passive income to supplement my business income. 

You lose now if you sell and if you rent you will need to supplement your tenant rent every month to cover your expenses.

Any investing you do will supplement your income now and after you retire so you clearly do not need much.

The middle class in the US is defined by having loans / credit to supplement your quality of life, like a house and car purchased with loans. 

You can supplement your own unit with Airbnb, although pay attention to the neighborhood as santa cruz has a moratorium on new vacation rentals, capitola only allows them on certain streets etc etc.

Sure, it's not cash flowing now but in 8.5 years it will be hugely supplementing my income. 

Travis- We have played around with the idea of me living in the home at first (as we are told you need to be a resident for these kinds of loans) and then using airbnb to supplement as much of the mortgage as possible.