For #2: In my experience, it takes a long time to go from "the basic question" to a well-founded statistical question for which analysis is appropriate.

For #3: The best managers and analysts will find ways to ask questions and meet in the middle between technical complexity and the business/science problem at hand.

http://www.openintro.org/stat/textbook.php

It's a free online statistics textbook, also available in print. I haven't used it extensively, so I can't vouch for its quality -- actually, I complain about it a bit in Statistics Done Wrong. But I've never come across a very good conceptual introduction to statistics, so this is roughly the best I know.

There are also amusing variations, like the cartoon guide to statistics:

http://www.amazon.com/Cartoon-Guide-Statistics-Larry-Gonick/...

If you find a useful resource, I'd like to hear what worked for you.