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.

I have a separate business I have ran here Blue Mound for almost 20 years, the house behind my shop went back to the bank, then was auctioned at xome.com where I purchased it.My interest is to acquire a handful of properties as rentals that hopefully will supplement my retirement one day.Bigger Pockets has been a wealth of information, I've spent untold hours listening to podcasts and reading articles, I want to say thank you to all of you that have taken the time to share your knowledge so patiently and generously. 

On the final check, which was a tiny amount for a bit of supplement, OCWEN said they wanted me to sign the check and they would pay contractors directly. 

Hey @Chris Conde, I'm not sure if it will help but I wrote an article on how I use FB fan page and Ads to supplement my vacation rental bookings.