(Disclaimer: As a past SIAI Visiting Fellow and current Bay Area resident, I've talked to Jasen about his plans, but do not speak for him or SIAI.)

I think you may be overextending the "boot camp" analogy a bit beyond the intended connotations of organization/discipline/intensity. That said:

Suffering is a big part of being a soldier and being physically active, but not necessarily part of being a rationalist and being mentally active.

Doing anything hard often involves fear, frustration, self-doubt, disapproval, sacrifice, and other sorts of pain. Not suffering in response to these signals, and not letting them overly sway your actions (giving up too soon, or not doing scary things) is really useful. Make no mistake, the intent of the course is not just to train theoretical rationality, but to enable people to do hard and meaningful things.

(I don't mean to say that causing suffering is an intended part of the course, just to state why I think learning to withstand pain is more important to becoming a formidable rationalist than it sounds like you do.)

Will you keep that for the group effects, or try and make the process as pleasant as possible? Is rationality training something that goes better when you force it, like physical training or unit cohesion, or something that goes worse when you force it? Will you try to manage/preserve the curiosity of students, and how? How skilled are you at detecting and manipulating the bounds of human endurance?

These are good questions.