I would say it is possible, but engineering the appropriate solvents sounds pain-staking. I wouldn't do this at cold temperatures unless you had a couple life-times or your low-boiling solvent is extremely volatile. Essentially this is a slow way to 'crash-out'. Slow in the case of gorgeous crystals is a good thing though. That's my ape level understanding of it at least(a physical chemist would scoff).
I would first try it at room temperature, after some time(a few weeks maybe) I would then try applying cold temperatures to induce crashing if it failed. This is because the low boiling solvent needs to be volatile for this 'migration' to occur.
The problem here is this in my opinion: picking the right solvents and not needing a chemical supply house to do so. A low boiling solvent dmt is poorly insoluble in is hard to find. Acetone, methanol, ethanol, DCM, Ether, Ethyl acetate, even light fraction petroleum ether, all solvate dmt pretty happily atleast at temperatures where they are volatile. While the higher boiling solvents such as toluene, xylene, d-limonene or what have you will still solvate dmt probably adequately so thats the easy part. If I think of something for the low boiling solvent I'll post back but it's not likely to happen, at least not easily.
A freeze precipitation works under different principles. Principles of solubility and a few other branches of the thermodynamics tree. As for crashing dmt out of xylene with naptha this is unlikely to occur unless as you said really cold temperatures are used. As I said above it would be painfully slow if it is even possible. At least that's how I envision it, experimentation is the only way to know for sure.