For me, I most often listen to something close to Option 3 (CDP to tube amp to speaker); I actually use a music server to play ripped CDs. This is not necessarily a quality choice, but a practical one. Most of my collection is CDs, primarily because newer classical releases are available ONLY in digital form. Fortunately, classical CDs are recorded and mastered to sound quite decent. Even re-releases from older analogue sources sound good in digital versions (e.g., many DG recordings have been remastered to sound much better than their crappy 1970-80's vinyl recordings). I tend to also listen more to non-classical music from digital sources these days from the server because it is so much more convenient than either CDs or vinyl.
For non-classical music, my very best sounding music is mostly found on vinyl--rock and jazz from the pre-digital era usually sounds much better on the original vinyl. I don't think this is so much an inherent superiority of vinyl as it is more the case of bad/indifferent mastering to digital. With some reissues, it may also reflect deterioration of the original source that accounts for the inferior reissues--some recordings just don't sound as good in any form of reissue.
If I had to choose between digital and vinyl as a source (purely an academic exercise), it would be digital because there is A LOT more music available in that format. I have MANY more recordings available only in digital format than I have vinyl recordings not available in a digital format.
For me, the choice of tube amplification makes a BIG difference in the sound. The particular tube amps I like have no comparable solid state offerings. But, I would not generalize that tube is superior to solid state because, to me, MUCH tube gear offered actually sounds worse than comparably priced solid state gear.
Hence, I arrived at Option 3 because the CD source would make available the widest range of music, and I happen to like and use tube electronics for amplification. I use either a low-powered single ended amp or a low-powered pushpull amp (I am not wedded to either camp). Last night, I got to hear again a particular OTL amp I have not heard in a while and it might be the very best amp I've heard (one of a kind 35 watt monobloc amp).