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I would spend your limited time and money just tasting wines from one region. Nahe is a smaller wine region just west of Frankfurt, and I've found the wines there to be good quality, with individual charm (in other words, without the sense that they are mass-produced). More info here
By all means, talk to locals: the people you're visiting, the clerk in ...
2
I'm not sure if you will find any Oktoberfest beer at the airport but they are available several weeks before "official" start in big groceries or beer shops. Hacker-Pschorr Oktoberfest Märzen, Paulaner Oktoberfest and Löwenbräu Oktoberfestbier were already available three weeks ago even in nothern Germany.
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