There are a couple of ways to learn about wine in general (the first part of your question), and there specific ways to learn about pairing wines. The pairing part is fairly easy so let's start with your first question about learning more about wine.

There are three ways for you to learn quickly and easily in my mind:

1. Podcasts: Fun, easy and free
a) http://www.graperadio.com/
b) http://tv.winelibrary.com/

2. Books: They cost money, but there are high quality ones out there

a) The Wine Bible
http://www.amazon.com/Wine-Bible-Karen-MacNeil/dp/1563054345/
b) The wRold Atlas of Wine
http://www.amazon.com/World-Atlas-Wine-Hugh-Johnson/dp/1845333012/
c) The Oxford Campanion to Wine
http://www.amazon.com/Oxford-Companion-Wine-3rd/dp/0198609906/ref=pd_bxgy_b_img_b

3. How To Articles: Free, fast and easy.

Mahalo has a number of great Wine how to articles to get you started:
How to Select Wine
http://www.mahalo.com/How_to_Select_Wine
How to Talk About Wine
How to Select Dessert Wine
How to Select Wine and Cheese

I hope this helps!

Finally, since you seem to be a big tipper why not just ask about specific wine pairing on Mahalo Answers and let the community do the work for you! For example, ask "what wines go best with a steak dinner?" or "What wines go best with grilled rare tuna?" Ask people to give sources and I be you will have a WONDERFUL experience.

Two good resources are winelibrary.tv and corkd.com. Hope this helps.

Start with your local wine retailer and tell him or her what you are trying to accomplish. I think a wine appreciation club might be a bit much to start with if you are a beginner. It can be very intimidating when you're first starting out to walk into a room of "experts" who are talking fifty thousand feet above your head. Unless it's a club that is geared toward beginners, you might want to wait a bit before joining so that you avoid potentially being turned off by the experience.

Also I recommend you subscribe to a wine magazine like "wine enthusiast" That is the one i susbscribed and it is pretty good
Cheers!

Also I recommend you subscribe to a wine magazine like the "Wine Enthusiast "

Cheers!

There are a few key tips to keep in mind when pairing wine with food.

1) What grows together goes together! Foods and wines that come from the same place of origin almost always make a perfect pairing. Think Manchego cheese with a Verdejo from Rueda in Spain, margherita pizza with a Negroamaro from the region of Puglia in Italy, or the pork and cabbage dish choucroute with an Alsatian Riesling.

2) Similar weight: pair light and delicate foods with lighter bodied wines so that one doesn't outperform the other and vice versa (heavier foods with fuller bodied wines). For instance, if you were to pair a brawny and tannic California Cabernet with seared scallops, the wine would completely kill the nuance of the scallops. Try a lighter, crisper style wine like an Albarino from Spain or a Gruner Veltliner from Austria. On the flip side, a Chilean Sauvignon Blanc will be completely overtaken by the high fat content and richness of a ribeye steak, so choose a robust red wine like an Aglianico from Southern Italy that has enough tannin and structure to cut through the fat in the meat and hold its own against the meat.

3) Pair spicy foods with off-dry, or slightly sweet white wines. Spicy Thai, Indian and Vietnamese dishes match perfectly with slightly sweet wines like German Rieslings or Gewurztraminers from Alsace because the sugar helps temper the heat in the food that typically comes from chiles. The sweetness also complements the sweet sauces that are often used in Asian dishes. High tannin red wines like Cabernet and Syrah will only heighten the sensation of spiciness and will very much clash with the sweet and spicy flavors in the food.

You can find great food pairing suggestions for a large selection of wines at http://www.plonkwinemerchants.com/