This is often the first question asked when I meet someone new and they find out I am a winemaker. It seems like a ridiculous question to ask. Would you ask a chef, "what food should I eat?" Well, maybe if it was in context.
Just as with food, wine selection is a personal choice. Wine has been produced for thousands of years, but the modern industry has become almost overwhelming diverse, especially for less-educated drinkers; differences in varietals, styles, production techniques, and places of origin only begin to describe the segmentation of the wide world of wine. Historically, wine selection was highly dependent on where one lived (if you lived in Burgundy, chances are you were drinking Chardonnay and/or Pinot Noir), but the ever-developing free-trade market gives most consumers the ability to get wine from all over the world.
So, let's try to help our new acquaintance in the quest for the right wine. My friendly and helpful self responds to this question with a series of my own, which may include "what kind of wine do you normally drink?", "red or white?", "do you like cask wine (box wine)?", "how much do you usually spend on a bottle?", "how much are you willing to spend on a bottle?", and "how many wines are you looking to buy?".
If you enjoy drinking cask wine, or any lower price-point wine, keep doing it. There is plenty of good quality, cheaper wine available (I've made a lot over the years actually), particularly during large over-supply situations like many wine regions are seeing in the current market. Why spend more money?
Unfortunately, wine drinkers fall victim to society's pressure to showcase status via expense. There is no need to spend $50 on a bottle of wine, and not everyone can afford to do so.
Wineries are subject to the simple economic principle of supply and demand just like any business; the increasing number of wine labels and supply of wine in today's market means that prices must go down to attract consumers. Savvy wine drinkers can find plenty of quality wines priced in the $11-15 range (if not even cheaper) depending on where you live and where you shop.
Drink wine that you enjoy. This is the most important thing I can tell a wine consumer. Even if you have the means to spend $100 on a bottle of wine every night, drink $10 bottles if you like them more. Everyone has a different palate; the key is to keep an open mind and continue to try different wines. Eventually, you will find what suits you best. Just don't forget, everyone's palate evolves and changes over time, so what suits you best can too!