We've examined lots of options and are genuinely doing our best to connect Webmasters with Googlers-in-the-know... both to answer questions AND get feedback and identify trouble spots.
We decided that interactions would be most productive by having folks like myself and Vanessa and search quality engineers set up and participate in our Webmaster Help Google Group... answering a (most typically frequently-asked) question once and having it viewed and helpful for thousands or tens of thousands of Webmasters.
Via the forum, Webmasters can get feedback and questions seen by the Googlers who are directly part of the Search Quality and Webmaster Tools teams... basically connecting with the source :). For instance, when I see issues that need to be addressed, I'm able to just walk a few feet to debug stuff with one of our crawl guys or someone on the spam team and so on.
Also, we are regularly hitting the road to speak on panels and chat with Webmasters around the world. At the most recent WebmasterWorld PubCon in Las Vegas, for instance, 25 of us Googlers were there. I'm posting this from Search Engine Strategies in Chicago -- again, along with more than a dozen Googlers. In just the last half a year, I've also chatted in person with Webmasters in London, Boston, Washington D.C., San Jose, and informally at arts events and other festivals and events in other cities.
We've also hugely updated expanded our help documentation in the last half-year... not to mention translated it into 18 languages.
Lastly, our Webmaster tools can help troubleshoot the vast majority of common questions.
There's more to come. Our team is growing (we just added a Webmaster Trends Analyst in Kirkland), we're committed to communicating in other venues and in greater amounts, and also supported by more powerful Webmaster tools.
And no, despite Barry's teasing in an external post linking to this thread, the best way to get a Googler response on our Webmaster Help Google Group is NOT to put my name in the subject. It's always best to use descriptive subject lines :)