Digital has come a long way in last 15 years or so and good digital these days can be hard to distinguish from analog. The best of each tend to sound similar to me. If I had to choose, in theory, I would prefer the best possible analog source to the best current digital source available. That source would be a large format RTR tape, not phono. In most cases, with most recordings, what sounds best will vary case to case. But digital is probably still not able to match the best analog POSSIBLE with technology to date. BUt in most cases, practically, it is so close that it really does not matter in practice for most.
In general tube amps may sound similar to SS amps but some tube amp sound might be quite distinctive and hard to replicate with SS. Its a different flavor of sound, not necessarily "better" though in this case.
SS versus tube amplification is an even tighter race to call. The best I have heard of both tend to sound similar.