Second question can be summed up by the timeless phrase "practice makes perfect". My wife likes to say that we are "functioning alcoholics". She says this tongue-in-cheek of course, but I'd like to take the notion a step further... I like to refer to myself as a "professional drunkard!"
Let's put it this way... I drink EVERY day. I drink, perhaps a dozen different wines, liquors, beers, daily, as part of my job. I then judge whether I (or my staff) can sell this alcoholic (though I do love dabbling with non-alcoholic beverages as well... one of my favorite restaurant projects was compiling a non-alcoholic soda menu for my more sober patrons) beverage at the price that a restaurant mark-up would necessitate. I taste thousands of wines a year. And, while I don't have a rating system which major publishing market houses refer to for their critical reviews, I do have a very simple rating system, which is my customers and my staff's appreciation of my choices. Sometimes I fail their expectations, but more often than not (and my restaurant sales will reflect this) I "wow" and excite my guests with new interesting varietals and styles that they're not going to read about in the major trade mags.
I will not sit here and tell you that I'm a classically trained Sommellier or UC Davis Grad. I am a simple, humble servant to the god Bacchus. My goal is to keep the subject of wine light, lively and conversational. I will not sit here and tell you I know everything there is to know about wine, far from it. And fuck the guy who tells you he does know everything there is to know about wine. That douche-bag is straight-up lying to you. The world of wine is too vast. It takes an army of magazines, bloggers, wine store clerks, websites, TV personalities to help us choose which bottle would be the absolute BEST bottle to drink with this evenings dining selection tandoori barbecued shrimp.
I have a simple approach to wine tasting, buying and selling. If I (or you) like the wine... it's a good wine! I don't care what Karen MacNeil says. That's my mantra, and I stick by it "If you like the wine, it's a good wine." We all get introduced to different levels of wine quality the more we consume. Your tastes will evolve. But there is no wrong or right wine... hell, it's all just fermented grape juice. Sure it takes on a magical quality that transcends mere alcoholic beverage. But the more mystique we add to the simple act of drinking wine, the more enjoyment we deny ourselves.
The wine world is too full of ego, conceit, misdirection and marketing... I'm gonna give it to you straight. I'll be tasting wines, and passing my thoughts onto you. And you'll give me plenty of feedback, I hope. And we'll all share in the wonderful joy of wine together, without the constraints of rating systems, trade mags, marketing power brokers, and wine-snobs.
I want you to get comfortable, sit back, pour a glass, relax... and know that whatever it is you've got in your glass, if it makes you happy... well, that can't be all that bad, huh?
(side note: I certainly use a little levity when describing my persuasion toward the drink, but I want to note that alcoholism and substance abuse are no laughing matter. I've seen to many friends die from heroin, and I watched my grandmother struggle with alcohol until her untimely death. I don't take addiction lightly, and if you or someone you know suffers from addiction, the best thing you can do is confront the disease. Some support groups to help: http://www.aa.org/, http://www.drug-addiction.com/)