How long did it take you to figure out that you could do that?
Saw their post on the forum - so not sure how to answer that - but I guess you could say it took me a month or so to notice the post.
How long/confusing was it to fund your wallet?
Not confusing at all - got some mBTC from Gavin's faucet to play with and within a week or so after that I had bought around 10 BTC from a BTC purchasing service (not particular good rates but very easy).
How much research did it take for you to find/configure your wallet?
No research at all (beyond an internet search for Bitcoin) - just downloaded and installed the software and then ran it (or did you mean something else?).
How long would it take for you to explain all of this to grandma, and Suzy in accounting? And would they be able to have it all setup, and be buying things in 10 minutes.. Like with PayPal?
Apart from the issues of using an exchange to get BTC I really don't think my mother (my grandparents have been dead for many, many years sorry) would stuggle as much as she did learning how to use Word.
As for Suzy in accounting my wife (who studied accounting at uni) has no troubles with Bitcoin at all and waiting for the blockchain to download (when using the Satoshi client) is the only reason she wouldn't be up and running in 10 minutes.