In my experience, all things being equal, a tube amp will impart more of a tube sound to the presentation than a tube preamp, but some speakers need ss power to drive them and in that case there is only one way to go.
If I'm looking for "Tube Sound", why would I put a Tube Pre in front of a SS amp?
I'm purposefully not specifying speakers as I would like to know in general terms the arguments for and against. So, to the degree that speaker characteristics could also influence the choice, please explain. FWIW, I do not know a phase angle from an impedance curve so I will try and educate myself as we go along. Hopefully, others may benefit too.