Brian K.:
Another thing I maybe should consider... what if i send out applications/letters to a few of these places, and they reject me coming to stay with them? I mean, that would sort of fuck up my plans for the next year or so, since i plan on taking a retreat..... Has anyone ever been rejected from residence from a place like this? Is it common? like maybe they ran out of room or something. Also note i have no physical or mental illnesses that would restrict me from being able to meditate safely.
If that's a concern, maybe try a shorter retreat first in the same tradition. I went to a 3 week and then 1 month retreat at TMC in San Jose, California. See http://tathagata.org/ The cost is $25/day and that includes everything. The food is vegetarian and mostly Vietnamese (the center is run by the local Vietnamese community), I found it excellent. It's part of U Pandita's branch of the Mahasi tradition and the Burmese Sayadaws who teach there are excellent teachers. The retreat is as hardcore as anything else.
The second retreat I went to there was led by U Pandita Sayadaw (who is now retired from teaching abroad). At the end of my only interview with him at the end of the retreat he suggested I go to a two month retreat at his main center in Burma. They won't refuse you on the application when the head of the tradition has invited you.
He was the only one who needed a translator, the rest of the monks do speak English, though with a Burmese accent. You can discuss arrangements to go to one of their centers in Asia with them and you'll get a taste of what a longer retreat in this tradition would be like while staying in the States. They'll also invite you to go to their centers in Asia at the end of the retreat. Consequently, when applying to an Asian retreat center you'd be able to list which other retreats you'd gone to in their tradition and which of their monks had recommended you.
I had a hard time of my first retreat because I had my own wrong ideas of how vipassana and meditation in general were supposed to work, despite good instructions and daily interviews with the teachers. Even with teachers who speak English as a second language, language issues are non-trivial, since they'll use technical terms in different ways and with different connotations than the way you expect them. I got through these issues before my second retreat there by working with Kenneth Folk to make sure my noting technique was correct and of sufficient quality and skill to get stream entry. I was able to get stream entry at TMC right before the end my second retreat. I think it would have taken a lot more time without Kenneth's help and even more time if I'd had to talk through translators to talk with the Sayadaws. It really is worth getting stream entry in the States and then going off to Asia once you know what you're doing and have done one cycle.
If nothing else, multi-week retreats can be very hard on the body, especially the knees and back. Since you're not supposed to do any exercise on these retreats (not even stretching, which I did a bit of anyway) other than slow motion walking meditation (which I consider more of a stress release valve meditation than any sort of exercise) it's good to do a shorter retreat as a dry-run before going on a longer one to find out if your body will have any issues and figuring out how to deal with them between retreats. Despite prior retreat experience and years of meditation, my first retreat at TMC was an exercise in meditating on leg pain, as was my one and only Goenka retreat a few years before.
You may also want to make an arrangement with someone to teach you how to do jhanas (Especially jhanas 5 to 8, the immaterial ones and without putting too much emphasis on nimittas. It doesn't matter how shallow the jhanas feel, as long as you know how they feel, can distinguish between them and know how to access them at all.) and navigate the review ñana that will happen right after stream entry. It's something that's best trained once you get to that point, rather than before. The TMC monks aren't so much into that. They really just want you to do noting, which misses on the special opportunities that you'll have during that ñana. Others in this thread have pointed out that it's good to prepare yourself with the best instructions possible before going on a long retreat with no internet access, I think you're sufficiently close to stream entry that one or two retreats should get you to it, so that you'll have the skills you need to do an effective longer retreat in Asia.
TMC has retreats every other month or so. They have a 3 week retreat that started a few days ago and they don't mind if you show up now for a partial retreat. The next 3 week retreat will be in November.
If you do go to TMC, I also recommend that you ask the office for the handout on the reporting format. The Sayadaws in the Mahasi tradition have a very specific reporting format and they'll explain exactly once. The sayadaws sort of consider reporting in the proper way a test of whether people are paying attention in their meditation and taking them seriously as teachers. If you go to some other Mahasi-style retreat center, it's worth getting them to explain the reporting format right away and making sure that you're crystal clear on it. Reporting properly makes a huge difference when it comes to the instructions that the sayadaws will give you. Interviews will be every day or every other day, so reporting is a big part of the practice.