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1. „wobei“ (at what) is derived from „bei“ of course, and the „wo“ doesn't mean anything here, it only serves to make it a question word. You'll find lots of question words created that way, for example „womit“ (with what), „wofür“ (for what), „wogegen“ (against what) and so on. 
So why is someone asking „Wobei können wir helfen?“ (literally „At what can we help?“). The reason is that Germans would use „bei“ to give a purpose, for example „bei der Reise helfen“ (help with the journey). 
In the end, saying „to help at something“ may be illogical, but „to help with something“ isn't much more logical either. It's something you have to get used to when learning languages.

2. Sie sollten = you should. Just like "möchte", this is an advanced form that we'll explain later.

Wie ist Ihre E-Mail Adresse? 
What is your e-mail address?

Er gilt als ein vertrauenswürdiges Mitglied unserer Gemeinde.
He is valued as a reliable member of our community.

Es gibt immer Mittel und Wege. 
There are always means and ways [of doing something].

Ist Bier teuer in Deutschland? 
Is beer expensive in Germany?

Sie sollten nicht rauchen.
You should not smoke.

Wofür brauchst du das?
What do you need this for?

Das ist zu teuer. 
That is too expensive.