What kind of financial/tax/legal advisor do we need?

We are small business owners who have been creeping along for years with a decent but not awesome accountant (business and personal) and no one else to advise us. We had a living trust done ages ago, but now I suspect the lawyer was not the greatest for various reasons. I feel like we need to be more mature about our current assets and future planning as we are growing older. We don't have much to speak of socked away for retirement but do own some income property. The accounting/tax/legal stuff feels very interconnected, but it seems you can only consult one specialist (tax or legal or accounting) at a time, like professionally these don't really cross over. Is that true?

I'd like us to be more aggressive with our taxes (meaning our accountant is very 'cut and paste' and does not seem well versed on the changing tax laws), learn how to put some money away for a rainy day and make sure our legal docs like a trust/medical directive are up to date. I'd like to find a combination of tax person/accountant and lawyer to work with. Does this kind of unicorn even exist? We would greatly appreciate some recommendations! Thanks in advance!

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I think you’re right about how people in the financial world tend to either go the CPA/EA (enrolled agent, meaning that they can do taxes across state lines) OR the Registered Rep (RR)/CFP. BUT my finance services rep (Nini Yang 408-464-7563) has her EA, RR, and CA Dept of Insurance. Understanding the tax implications about investments and planning is VITAL! I worked with two agents before finding her and she’s the most comprehensive, well rounded financial services person I’ve found. 

I work for a small law firm that has various attorneys specializing in estate planning, tax, real estate and business law.  And my mother was (she's retired now) a CPA specializing in personal tax and estate planning, in an accounting firm where some of her colleagues also handled business taxes and financial statements.  So you can certainly find "crossover" help, from partners in the same firm if not always from the same individual lawyer or accountant.  Also, you may very well need more than one specialist consultant - say, a lawyer to help you with the living trust and managing the income property, an accountant for tax planning and preparing your returns, and an investment advisor to consult about saving for retirement - but those people can, and very often do, talk to each other!  Sometimes even refer each other to clients, so if you find a CPA you like, that person may be able to help you find a compatible lawyer or vice versa.