I was in a similar vinyl dilemma a few years ago. Indeed there is more care and feeding involved in a vinyl system. However, after deciding to take the plunge, I have found the rituals involved to be pleasurable. The payback for me has been a more organic and satisfying sound.
With modern equipment, and record cleaning machines, the pops are rarely noticeable and when they happen, are not really objectionable.
Prior to vinyl, I had a Wadia 861 driving my CAT amps direct. Going to vinyl, I was obviously forced to purchase a pre-amp and bought a Supartek Chenin (with phono). I decided upon a Galibier turntable and Tri-Planar arm. This combination has been simply wonderful.
Fortunately, I had kept my LP from my youth, and have added several hundred primarily used albums to my collection. I find fun in hunting for used vinyl both locally and on the net.
Upon acquiring my vinyl rig, I found myself using it 95-99% of the time! With a $6K CDP essentially sitting idle, I decided to divest myself of it and move into the world of PC audio by purchasing a MacBook laptop and Wavelength Brick Silver DAD. I havent missed the Wadia, and now have the best of both worlds. Ive gotten off the CD playback upgrade merry-go-round and if I choose, I can enhance my digital playback by simply acquirng a DAC. BTW, I believe that PC Audio is the future of digital playback. For me, it has been that good -- both sonically and from a spectacular convenience perspective!
You do have a significant investment in CDs and it would be time consuming to rip them to a HD, but Im getting ready to send my approximately 650 CDs off for just that purpose. While over the years my son and I ripped most all of the tracks we liked from the collection into WAV files, they lack tagging info, and there are times I would like to play an entire CD or tracks other than what we ripped.
But I digress. Until I heard vinyl playback in my room/system, I wasnt necessarily smitten with the sonics that I had heard at a local dealer.
I was fortunate enough to have my turntable manufacturer passing through my locale trucking a table from Colorado to N.Y. He brought a rack, the tt, placed it in my room and couldnt energize the phono he brought. Believe it or not, I hauled one from storage a Phase Linear pre-amp from the 70s fired it up and listened to a Galibier tt, Graham tonearm and Denon 103R. From the first few minutes of the first LP, I was sold, and the rest is history.
I have what I consider to be an heirloom turntable, and I love everything associated with vinyl playback. While superb quality recordings sound, well superb, one of the things Ive found surprising, is Rock playback. I like most all rock material better on vinyl. It has immensely enhanced my critical listening repertoire.