I have read a couple topics with similar concepts. So if swim takes his dmt saturated naptha and put it under vacuum to evaporate the solvent and collect in a cold trap is it possible the dmt get carried over with the naptha?

with a rotary vane pump, yes. it pulls a fairly stout vacuum.
naphtha has a low boiling point; a diaphragm pump may be more suitable for that particular application.

If I was able to regulate the vacuum and constantly measure it should be okay? I also want to collect my solvent in a cold trap, I guess it would be like a distillation? What if it was in a solvent like xylene? I was reading a thread which you and some other members were discussing boiling point of dmt, which suggest that the boiling point was around 350C for very pure dmt. So does the dmt not have to reach its boiling point to vaporize and travel over with the solvent?

if you have decent control over the pressure via regulator valve, to achieve gentle boiling without bumping, you could probably separate it effectively. bumping is the real issue, avoid it and it should be ok.

What if the solvent is xylene, with it's higher boiling point would it still be possible to separate it from the spice with out the spice coming over?

also if your solvent was already cold you could minimize the bumping even under very low pressure