[others are welcome to reply, too...I'm just tagging the thread so Jeff knows to chime in]
Jeff, I'll go first (anyone with other questions for Jeff, please start a new thread!).
As a chowhound, I rarely enjoy balanced, carefully composed meals in restaurants, because I always want the very best stuff the kitchen does, even if the total effect isn't harmonious. I realize that's non-ideal, and I do appreciate harmony. But I appreciate isolated experiences of vast deliciousness MORE.
The problem is...wine. Following my natural instinct, I scan the wine list, eliminating the stuff I can't afford (usually 75%, alas), and try to find the most delicious wine among the remainder. And this often adds a fatal extra element of disharmony. I can live with disharmony of courses (or even a slice on the way to the restaurant), but wine goes WITH things, so you've GOT to match, lest your robust cab savage your raw oysters. You CAN'T look for the single most delicious bottle, you've got to think harmoniously.
Now, at a big blowout, it's easy to justify ordering a few bottles for the table to mix and match with various courses. Fun. But chowhounds eat out on a more everyday basis, and often refrain from ordering wine because finding a good wine that's priced reasonably is a triumph...and having it match halfway harmoniously with the various items would be a miracle. So, I only order wine at blow-out meals or at places with wines by-the-glass. That is...not very often. And I'd LIKE to drink wine more often.
How do YOU strategize in this situation? Can you give us some savvy tips for situations where you don't want to spend a ton, don't want to drink a ton, just want some decent vino to go with your food, but you've got to do serious triage on a fussy wine list (re: price and quality)?
"Marry someone wealthy" would not be a helpful response.