TidBITS, started in 1990, is an online newsletter and Web site about all things Mac and Apple. They cover a wide variety of topics from business uses of Apple products to troubleshooting to "just for fun", plus a lotta other stuff. They have a website, a mailing list, and you can join TidBITs as a member for access to more good information written by experts for us mere mortals. To me, this is the most user-group like resource I've found.
Small Dog Electronics is actually an Apple retail operation with four stores located in the state of Vermont. They have an active blog and different newsletters to which anyone can subscribe. They are definitely user-friendly.
9to5Mac was born in 2007 between the announcement and the launch of the iPhone. This site focuses on breaking news and analyses, but they publish reviews of devices and apps as well. (Two companion sites, 9to5Google and 9to5Toys are related to 9to5Mac but I haven't visited them.)
MacRumors is the slightly more hyper cousin of 9to5Mac and focuses on - you guessed it - rumors of upcoming Apple products, services, and activity. I take everything I read here with a grain of salt, but it's never boring.
Cult of Mac is a daily news website that follows everything Apple. They post news, reviews, how-to's (hey, that rhymes!), and other info. I never found a lot of newsletter material here (most of what they posted didn't seem of interest to our user group members in my opinion) but it's fun to read.
Finally, I've been pleasantly surprised how often I've found truly helpful instructional videos on YouTube for doing things with my Mac. One of my favorite YouTube channels (is that what they're called?) is Mac Help for Moms. Whenever the guy's mom had a question, they made a video to answer it. Very user-friendly. Just go to youtube.com and search for "Mac Help for Moms."
Hope that helps get you started!