I think the title of "pre-amplifier" has a very specific meaning in stereo equipment. It is intended to "collect" all of the various sources that might be connected into a system and provide the primary signal amplification. That means that it has switching to handle multiple source inputs and that it outputs to a standard that can be used to feed a power amplifier.
In real practice, a pre-amplifier provides voltage signal amplification, only - with little to no current amplification (sometimes called buffering). That usually means that a good pre-amplifier has very good S/N specs. It is not intended to power a load of any substance, however.
In common stereo systems, the headphone out is usually provided in the pre-amplifier section. This was typical because many headphones were often regarded as very high-impedance loads with little to no current draw (>600 ohm or crystal sets?). This changed through the years as dynamic headphones became popular with much lower impedances. Headphone out connections were often provided with their own separate amplifier circuits, or in the case of many receivers (a pre-amp and amp combined), perhaps a cheap resistor off of the power amplifier output.
There are many flavors of pre-amplifiers - some with headphone out capability, some not. It's really up to the user to determine whether a particular pre-amplifier is really an equivalent of a dedicated headphone amplifier.
As to your specific questions, I think orthos (Fostex TR-50rp's) are a poor choice to connect to a pre-amplifier. Most orthos require lots of current - even a power amp, period. That's not the specialty of typical pre-amplifiers.
About DACs - you will find with a few exceptions that most "tube" DACs are simply DACs with a tube-flavored amplifier circuit applied to the output
after the primary DAC circuit. Most, if not all tubes (and I am a tube proponent) are simply not able to provide the super-low-noise, current-to-voltage conversion that most quality DACs need. Tubes were primarily designed to amplify voltage and use very high voltages to attain reasonable S/N ratios. Conversely, DACs output miniscule voltages and currents. You really need some transformers in the circuit to apply tubes directly to a DAC and both introduce significantly more noise to the miniscule DAC signal.
For the same reasons as above, you won't see many tubes applied to a phono pre-amplifier, either.
This will probably cause a flame war, but yes - a dedicated DAC of some sort will probably give you better sound than your motherboard's output or a Creative Labs SoundBlaster.