TUBE....Starting with Power or Preamp ?

I've been looking at this forum and found "MANY" loves tube gears a lot. It makes me want to enter the "TUBE" arena but I'm not sure which one to start with between Poweramp or Preamp. Could anybody have an experience answer my question below? If I have only one tube equipment to start,.....

1. What's the sound would be using SS Preamp + Tube amp?
2. What's the sound would be using Tube Preamp + SS amp?
3. Which way is a better approach?
4. Which Tube Poweramp or Tube Preamp is great for around $500-$800 used?

My music preferences is Acoustic Jazz with lots of details and some drums + percussions. I like the music that is sweet, very involving and real. Any suggestions would be very appreciated?

Supakit S.