What wines do you avoid?

I avoid wines that I know are easily accessible for the recipient, like something they could buy from the closest corner store. Go to your local wine shop and talk to the staff. The good ones have curated their selection by tasting everything on their shelves. They’ll point you in the right direction.
I also stay away from wines that appeal to a very specific audience, unless I know for sure that the recipient is a fan. For instance, it would be a rare occasion that I would gift an alcohol-rich fruit bomb, or on the opposite spectrum, a skin-contact Georgian orange wine. Amphoras are cool, but not everyone “digs” them.

How much is too much or too little when purchasing wine as a gift? 
You probably want to spend more than two dollars, but I wouldn’t worry so much about the price as the thought that went into the purchase. If you know the host, or they are an adventurous wine drinker, I’d ask your wine shop about up-and-coming wine regions or interesting varietals. I love introducing people to varieties that are new to them, such as Trousseau Gris grown in Sonoma’s Russian River Valley or Teroldego from Trentino, Italy. A little effort says so much more than emptying your bank account.