Does anyone know an investor friendly tax/attorney person that I can talk to and can guide me through this process? 

If you use the Heloc option and decide to rent it out, don't forget that property (or you) will have to cover both your primary and secondary position notes.I don't personally see Marin being a great mid term market.

It is my understanding that people refinance and then use those funds other ways (personal living, investing, some to buy another property) as a means to minimize tax obligation. 

We have been able to get some great deals simply by doing extra research that the average person wasn't willing to do.

Together, we can harness the power of technology and creativity to make significant strides in our personal and professional lives.

It sounds like you've done a great job in investing in yourself and taking personal risks. 

Personally I like the Section 8 program when the property is located in a super poor area with a ton of blight and crime.

When I partnered with friends on a multi-unit property a few years ago, we chose individual umbrella polcies from our personal providers.

Go in person to the planning department and talk to them.

If you did not like that experience, maybe you should try a smaller company to get a more personalized service experience.