Your idea of using acetone under pressure is very inventive, and I wouldn't be surprised if it works. Pure acetophenone works, according to an abstract I saw once. Although shaking with the acetone will displace some of the air with acetone vapor, you could replace all the air by blowing propane, butane or carbon dioxide into the pipe before sealing it. Butane may be the most convenient. The only problem I see with your method for the hobbyist is that not everyone is as safety conscious as you are.
When I researched a better way to make tryptamine my goals were to use cheap OTC materials and to make the procedure as simple as possible, not for my own sake but for the benefit of the people who use this forum. I started with Drone's procedure using xylene and butanone, which are highly available, but it didn't work. I didn't know that menthol or limonene were commonly available, so I tried other solvents, and finally found success with xylene and turpentine when using an enone catalyst. The smell of these solvents, or the time needed for the reaction, were not major concerns. All the solvent except what evaporates from the crystals can probably be used directly for the next batch. There was no smell during the reaction. Tryptamine may not crystallize from menthol, in which case extraction would be mandatory rather than optional. If I use an Erlenmeyer flask for the reaction, all I have to do for work-up is pour out the solvent and leave the flask on its side for a few days until the cake of crystals on the bottom is dry. As long as this reaction requires heat, I don't see how the procedure could be further simplified.
I just checked out the product from using turpentine. Even though it had several days to dry in a stream of air, it still smells or turpentine and is a bit gummy. The yield is above 90%, but it remains to be seem whether further drying will reduce this. I suspect that this turpentine may have a non-volatile residue and will require distillation before use. Limonene might be a nice alternative.