The short answer is yes you will likely trigger a tax consequence for selling your property. 

Most properties have gained considerable value since their acquisition or refinance.

Or get with an expierenced realtor, commit to 1031, and increase portfolio by considerable margin and sacrifice cash flow now?

Hello, Mark Svendsen, based on the information provided, here’s my analysis and some considerations regarding the trustee's decision and your options:1. 

Hello Jared Schott, regarding your situation, here are some considerations and options for managing the $280,000 gap: Second Mortgage: You can seek a second mortgage or home equity loan to cover the $280,000.

Cities like Pleasanton, Livermore, Dublin, San Ramon, Danville, Castro Valley are worth consideration. 

Thank you for the insight and I will strongly take this into consideration.

If not, this might be a consideration to having a low down-payment for a property.

I pulled the trigger on one of their Bennah Oaks properties in December.

Even if delivered vacant it can take a considerable amount of time to legally de-regulate a stabilized building and it mostly requires you to have the units vacant for a period time (no cashflow).