Hi Lyle,
Long time listener, first time caller. This is of course a fascinating and layered topic, and as a west coast somm i thought i'd toss in my two cents.
Firstly, i feel like i must offer at least a rudimentary defense of restaurant wine prices in San Francisco, as i think we deal with certain issues that New Yorkers don't. Minimum wage here is just under $10/hour, a fact i LOVED back in the server days (especially moving here from Boston, where i got $2.63 an hour, ouch). Also, last year we had a well intentioned but somewhat sloppily executed "Healthy San Francisco" universal healthcare fee dropped on businesses here. While i won't bore you with the complete details, the end result is something like an extra $1.34 per hr per worker! Not a huge burden in a retail store, but in a fine dining restaurant paying servers/bussers/dishwashers/hosts/etc what is basically $11.50/hr, you can see where i'm going with this. The beverage department is a no-brainer way, nay a neccesity, to ensure survival. So yes, our wine by the glass programs are designed to maximize profitability, and cult wines (i don't mean that in the awful, Screaming Eagle fashion, more like the Rouget/Dugat/Vogue/Vega Sicilia/Gaia sense) will hurt those who dare to tread, but the downward economy combined with the infant dimwit cum foodwriter we're saddled with has brought the issue of affordability to the forefront, and everyone has had to get creative to cope. What you see are a lot of "40 under $40", "White Wines $60 and Under" etc...
It's in these categories that i've actually had the best luck turning people on to the rustic, weirdo wines that i like to drink, seeing as i'm simply unable to buy bottles in a restaurant over $75 or so (yes, it is hard to reconcile business with my personal taste and desire, but we ALL work under Wine Directors who set markups at some point in our careers, no?). Thank god for Kermit Lynch and North Berkeley!!!
Regions that kill it for me as far as value are concerned are, in no particular order
*Languedoc/Roussilon/Central-Southern France- St. Chinian (Mas Champart), Cahors (have you had the Clos la Coutale?! Cheap spicy and delicious), Minervois, Madiran, Cotes du Rhone and their various and sundry Villages (I think Feraud Brunel makes wines that WAY outperform their price!!). Yeah, I know that some of these wines are insanely rustic and/or unfamiliar to your regular Cali Cab drinkers, but I think these people need to understand that if they want to spend $35-50/bottle in a swanky joint, they might just have to travel out of their comfort zones and let the folks who spend 60 hours a week humping boxes and processing invoices and tasting loads of awful crap just to find one good Russian River pinot guide them toward some tasty juice. Imagine if no one had ever turned you on to Mourvedre? Life without Bandol? No thank you!
*Beaujolais- God this can be a hard sell at first, but i've yet to see an unhappy face at a table drinking their first Lapierre or Foillard.
*Burgundy-HA! Get frack real. I've become an expert on Marsannay, Fixin and Ladoix just so I can feed my desire to sell Burgundy to the masses, but who am I kidding, these wines are still at least $65. I think Audoin, Chevalier, Gay, etc are doing a nice job. I just wish i could drink Chambolle instead of Chorey...
*Loire- You're SPOT ON about Dressner. Freak of the week or not, i'm always reassured when i see the Louis/Dressner sticker a bottle. I think there are still good buys in Sancerre and Pouilly, but with a little nudging we've had success with Quincy, Jasnieres, Montlouis and Cheverny. And i think it is the duty of any good somm to identify potential acolytes and promptly start them on their journey towards Huet. Today Cheverny, tomorrow Le Mont!!! Oh, and let us not forget Bourgeuil and Chinon, yum.
Well this was supposed to be a quick response, now it has ballooned out of proportion, but i guess what i'm trying to say is that a good wine department can offer heavy hitters AND sick deals, it just requires a well trained staff and owners willing to invest enough capital to cover all the bases. Oh, and as for putting a bunch of dead in the water, faded wines on the list, that just sucks! I like shopping end of bins as much as the next guy, but often times there's a REASON that 01 Verdicchio is only $6/btl

Cheers!