Just a few points on what has been said (thanks for all the input so far!)

I don't think that the vapor/smoke would have to pass through the oil very long since the thc is being released from the ingition/vaporizing (burning). You have to simmer the cannabis in oil for a long time to release the thc since it is not being combusted. With this method the thc is already out and active from the cannabis and just needs to be collected by adhereing to the oil.

Also as far as running the vapor through an "oil filled" chamber is not too tricky at all, some vaporizers even come set up that way so the the vapor can be filtered through a water chamber for extra filtering and cooling such as the Aromed vaporizer. You just need to take a whip style vaporizer remove the hose from the whip and attach a new hose that goes into a water chamber then connect the rest of the whip that you inhale from into the output part of the water chamber.

I really like midlifecrisis idea but would not be sure about trying it myself for the first time as it sounds like you would not want to mess up with neutralization etc. Also I am interested on how you would ingest it once it is made.

TheavidonE