T A V:
Once concentration can become established, the rest is a matter of insight. And presuming a clear mind as the ground for insight to arise, it is possible too achieve that despite the condition of having to rely on medication to stabilize the mind. The supervision should help keep things from going off the track.
What level of concentration do you suggest? Mastering all eight jhanas? Being able to attain to eighth jhana? (is this impossible for someone who is not even a stream-enterer?). Would mastering a lot of jhana be more helpful than say mastering a tai chi or body practice? (You may not know the answer to this if you are unfamiliar with such practices). Should I put equal effort and time into both? Should I focus on jhana first? Should I forget jhana and dive into body practices?
In order to begin practicing insight meditation, I have found that while being able to master the initial four levels of absorption can be quite effective in helping to condition the mind with concentration ability, that even just being able to attain a level of
samadhi just lower than absorption seems to also be an effective state for insight practice to take place.
To clarify this a bit, the absorption level of
samadhi would be along the line of
appana samadhi, or "fixed concentration" wherein the mind becomes absorbed in the meditation object, with all the subsequent jhana factors following: meaning
vitakka (directed attention),
vicara (sustained attention),
piti (rapture or elation), and
sukha (pleasure or joy). Just below the
appana samadhi level is what some have termed
upcara samadhi or neighborhood concentration (also called "access concentration").
Upacara samadhi would be a sufficient level of concentration to begin performing insight meditation. As long as you are able to focus the mind on an object or subject for 3 to 5 minutes without the mind wandering or without unnoticed mind wandering, then you should be on solid ground for
vipassana to arise.
Upacara samadhi would allow for this, in my experience.
T A V:
I feel I am very good at staying stable meditating on several hours a day, so it's no problem there. Also, concentration practices, of any duration, are no problem for me. They keep me very healthy and sane. . . . I may have to spend considerable time developing concentration. . . This is going to take considerable discipline and patience on my part...
I could get really into the Reggie Ray body-work stuff that takes meditation out of your head and into your body. Over-focusing on visual and auditory sensations is probably not the best idea.... I could look into Tai-chi...
Honestly, the only thing I can immediately think of is to move into the body and do lots of concentration to where I can do insight practice out of jhana so my mind stays calm...I'm not sure how strong my concentration needs to be to do this, or if it will be effective. But it would be all I know to try...
It sounds as though you are taking a balanced look at this, considering your condition. If you feel comfortable with the Reggie Ray material, it may be a good compromise practice which may be very helpful and effective for you. Using that practice (or even Tai-chi) as a base, you could work into developing deeper levels of concentration during sitting meditation which should help to develop the requisite level necessary for effective insight practice. You will likely need some instruction on what to look for during these insight meditation sessions. Starting out small and simple, though, and building up later to more complex subjects should help you gain confidence in your abilities in this.