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I added my business email account to Gmail. however, I find the standard method of changing the 'from' account (the pull down menu for each mail) to be tedious and error prone.

I'm looking for a method (or a plugin \ extension \ ...) That will allow one of:

  1. automatically select the from address based on the recipients
  2. change the default from address in one click (that is - all mails composed in this session will use the same account - until switching back)
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Not sure it's an answer to your problem, but in Settings>Accounts and Import I have the option "when replying to a message" and it has "reply from the same address the message was sent to" - which cuts down significantly the number of times I need to change the from message. – Peter Boughton Oct 5 '11 at 1:38
You might also consider creating a greasemonkey script – JMax Jan 19 '12 at 10:14

You can go to the Settings> Accounts and Imports and set the settings as shown in the screenshot below:

enter image description here

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