This can be an ongoing effort, otherwise it becomes too much of a burden and therefore difficult to accomplish. Use EAC to rip your CDs. I think it's one of the best applications there is for the purpose. Say, 3-4 CDs a day. Use image search to download album cover art which can be kept in the same folder as the ripped songs. This is much faster than EAC's in-built image search function.
I have gone through this exercise and I am really glad I did it (may be only some 20-30 CDs remaining), as CDs scratch due to carelessness and accidents. And then there are good friends who don't know how to return borrowed CDs. Having a copy makes the pain more bearable. Nowadays the first thing I do on opening a newly bought CD is to rip it. That's the best condition the CD will ever be in one's possession.
Once you have them as files, it is a question of using a good upsampling DAC to play them from your digital transport of choice. I would suggest something that does 192 kHz (or higher).
Do make sure you have a backup disk. A big (form factor) 1 TB Seagate serves as a backup for me. This is hardly portable and that's a good thing as there is less chance of damage due to movements and shocks. A smaller 500 GB and a newly bought compact 1 TB are my primary drives now, and reside permanently in my bag. I don't have a computer based playout yet but I am fairly ready with the content to play