Our goals are to help other investors with buying and selling properties where an agent is needed, and also to gain better control of our financial future through investing.

We're not going to leave active duty, dual pensions at 38 and 42 will help our future growth.

I crunch numbers on deals before I view it to see if it meets my goals financially for 10 years, 15 years, 30 years.

Mostly looking to build assets/capital for future passive income.

I'm almost positive that the tenant will have a different financial issue going forward, but it may be in another aspect of their life.  

@Allen Fletcher is right on in his assessment of the actual tax being dependent on past use (actually 500K tax free is the top exclusion if you're married and have lived in the property for 2 out of the last 5 years) and future strategy (depending on your path you could exempt all or part of the tax in a 1031 exchange).Your accountant paints the current picture better than anyone.

Operate as if a great deal may be right around the corner and be prepared to walk away.this is not legal advice, i am not a financial advisor, or a CPA

If you are possibly interested in working with me in the future, or even keeping in touch just in case I may be able to help you find exactly what you are looking for, please drop me a line!

However, the benefit of markets like Oakland is that the financial barrier to entry is substantially lower. 

Sounds like you have a potentially good thing going if you rework the financials.