I generally agree with the above post. You can now buy a -very- adequate double DIN radio to fit your stock dash that includes Bluetooth and all the basic features for a reasonable price. Even name brands aren't expensive for their lower tier products.
I've bounced back and forth on maintenance. I enjoy working on things if I can do it on my own schedule. When too much breaks at once it stops being a fun distraction and starts being just one more thing on my plate. At that point I'll farm things out to a local shop I trust as needed.