Disclaimer: I grew up with technology and was encouraged to understand it by my mother who is a computer person.
I have worked in IT for 12 years doing what I consider to be everything from easy to very mildly challenging work. Here's my philosophy on consumer level technology.
Here's the good news: Someone/somecompany has already done their best to make whatever you're trying to do work. Someone on the internet has probably already ran into the same problem and a discussion, including an answer to your issue, is probably as close as a google search. Things are constantly improving, if you wait long enough your pc will one day be as simple to operate as a toaster.
Here's the bad news: There is plenty bad advice, harmful software, and thieves trying to steal your money when your trying to resolve an issue. There are sometimes red herrings, as we trust computers more we are less likely to realize that their lying to us when they fail in an unexpected way.
My advice: Build on your successes with technology and only worry about the parts that are important to you. And if all else fails, just stick around and its bound to get easier.
