Call SimCom and specifically ask for Dick Goethe as your CE500 instructor - he's retired TWA and doesn't have much time in the Citation...but he's an EXCELLENT instructor. Also, if you haven't done so already verify that SimCom will do a PIC type without 1000tt for your colleague - I know FSI won't but don't know SimCom's policies.

For your first jet type rating, with no previous time in type, and a copilot who is also low-time with no jet experience, 14 days nonstop will *not* be too long for training. Now 17 days for a CE525s rating with 61.58 check, after having a CE500 type and 400+ hours in Citations...THAT is too long!

$25K is high for a Citation II with $2M liability...but actually quite reasonable considering pilot qualifications. Many 1000tt pilots going into Meridians or Mirages from a 4-place piston have first-year insurance bills that high or higher...and after about 400-500 incident-free hours you should see your insurance expense be cut by 30-40%.

If you do the WAAS update to the plane's existing GPS units you may not just need the boxes updated - you may need new antennas and wiring. Not cheap, but much cheaper than a spanking-new install. You'll want this done during the pre-buy if it needs to happen!