[UPT grading]

The IPs are supposed to grade you according to the course training standards listed in the syllabus. Unfortunately, the grades they give you aren't as black and white as what the syllabus states so they end up being pretty subjective. Check out the T-6 syllabus and it should give you an idea of what they're looking for (start at page 13).

http://www.t6driver.com/jsupt/jppt_jsupt_syllabus.pdf

[Information on PIT (Pilot Instructor Training)]

I'm going through PIT right now and it's currently scheduled to last 3.5 months. It's looking more like 4 months. If you're a tweet IP coming to RND for PIT then you go through the transition course which is considerably shorter. If you've never been an AETC IP then you have to go through the PIT program. Check out T6Driver.com for more detailed info on the PIT/Transition programs.