Need serious help with setting up home theater etc.?

Our TV is ancient (1998), my stereo receiver is from 1999, our DVD player died this morning. I am tired of the set up with several remotes etc. What we have: ROKU, Logitech Squeezbox (in garage), iMac with all our music in iTunes (in kitchen), Apple Time Capsule. Would like in living room: new TV, new DVD player?, internet radio, access to kitchen iMac's iTunes. Our speakers are old too, does that matter? I feel like I am stuck in a 1990 A/V cl...How do I converge all these things? Is logitech my answer? What about DVDs? We don't watch network TV, nor have cable etc. We rely on DVDs and our Roku for TV watching. Can anyone suggest a new setup? TIA