My choice would be for tubes in the preamplifier first as that is where any harshness would be generated, if, and only if the tube preamp or hybrid preamp has been designed to eliminate some of tube circuits usual major flaws, so that the tube unit does not actually make things worse.
The basic engineering purpose of using the tube is that the summing node of input and feedback on a reasonable tube circuit will have in excess of 200 volts of headroom before overload. A typical solid state device circuit will have 0.2 volts or much less headroom before the feedback loop clips and fails, all other things being equal.
Of course all things are not equal. The tube has weakness in having a high output impedance, low drive current, and significant load sensativity depending up the circuit design. That means tubes don't like to drive real world loads unless you give them lots of help. So, all other things being equal a tube circuit with high overload capability but bad drive capability might sound better or worse than a solid state circuilt with bad feedback loop overload capability but good drive capability. Actually, we suspect that most of the purple prose about tube sound and solid state sound over the years is simply jillions of efforts to actually described these effects as they relate to the listener musically, without the listener really knowing what is causing the effects he is hearing. Much like the six blind men and the elephant, multiplied times ???
Anyway, we think we are getting a pretty good handle on how to use a tube for its superior overload capability but without the tube getting into drive current and impedance issues that would detract from its performance. We do this with our Ultra circuits with a patented transimpedance amplifier design, using a small signal power mos-fet as part of the vacuum tube, providing a two piece device (along with some passive parts) that has high feedback overload immunity, low output impedance, high output drive current, and no load sensativity at all.
To make the new Transcendence Eight all tube preamp work as amazingly as it does, the approach was to provide each half of each tube with its own isolated high voltage high speed analog power supply regulator so that the supply impedance is a small fraction of an ohm broadband and there is no interaction between sections through the power supply at all. It appears to have given the tubes "a big shot of steroids", and we think the T8 will hit home runs for you even driving difficult solid state amplifier input impedances.
Both of our approaches seem to work very well, but of course the T8 still has a bit of that "tube like" character in its sound. Is it right or wrong, I just don't know, but it sure sounds lovely.
Frank Van Alstine