Lou...there is some very good advice here, and this can be somewhat overwhelming even for those of us very committed to these solutions. Many of us have tried many of these solutions, so the good news is there is lots of good advice available.
Some other feedback from you that could help narrow down some of these recommendations...
Is budget a consideration, and if so, what is your max to get you to a good solution?
Do you consider yourself kind of tech savvy or would you prefer more of a set and forget solution?
Do you have the time and patience to burn all your important source material to digital, or would you pay a service to do it, or would you just skip that and have your analog and digital (CD) sources still available when you wanted them?
How important is ultimate sound quality vs. convenient musical listening?
Do you like random music presentment like Pandora or FM radio, or do you prefer to either select and listen to the album straight through, or select individual tracks for a "mix"?
From those answers you will be able to get more specific solutions that might best meet your desired outcome and point you to some deeper investigation.
Some other feedback from you that could help narrow down some of these recommendations...
Is budget a consideration, and if so, what is your max to get you to a good solution?
Do you consider yourself kind of tech savvy or would you prefer more of a set and forget solution?
Do you have the time and patience to burn all your important source material to digital, or would you pay a service to do it, or would you just skip that and have your analog and digital (CD) sources still available when you wanted them?
How important is ultimate sound quality vs. convenient musical listening?
Do you like random music presentment like Pandora or FM radio, or do you prefer to either select and listen to the album straight through, or select individual tracks for a "mix"?
From those answers you will be able to get more specific solutions that might best meet your desired outcome and point you to some deeper investigation.