Hi there Ed,
First of all, welcome to the group! 
1) How many days after kickoff do you spend in CAD?
The goal is usually to get all parts to manufacturing in two weeks.
3) This will give 1 week for manufacturing then at the start of week 4, you're building. Driving and testing should really be at least by week 5. Usually this is in stages, since most teams will have a base design figured out before the competition, then adapt it for any special considerations given the challenge and may even have it built by the end of week 1.
2) CAD never seems to be complete! After major components are designed and detail drawings are complete, they usually need to complete the BOM's and create any necessary assembly drawings. Most of the designers are used in the assembly of the robot since they know it best. Most of the time fixes and adjustments are required.
I hope that gives you a decent idea of what happens. Stay tuned, because I think we'll be having some webinars hosted by PTC real soon! 
Josh
