First off welcome
I too am in the computer business sort of
I work on ATM/Frame Relay networks so I know where you are coming from.
Now for your questions.
Your first two weeks are going to be the hardest part. You are correct on caffiene raising insulin levels. Try as best as you can to lay off the caffiene products.
Your first two weeks you will go through withdraw. This will cause fatigue, headaches, dizziness, and a pretty over all crappy feeling. I would highly recommend you drink 64 oz of water plus 8 oz for every 25 pounds you wish to lose. Make sure you eat lots of healthy legal foods! Try to get plenty of sleep as well. This will help offset those headaches and icky feeling. Make sure you take your vitamins and supplements he recommends. If you don't have them yet, hold off on starting until you do. They really help the headaches and muscle cramps.
For ketostrips.....use them as a guide, not the gosspel truth. Many things affect them and they frustrate most newbies. Go for first thing in the morning to start with. Reason I say this is because water consumption, excersize does effect the "darkness" of the strips. Once a day is plenty. Don't drive yourself nuts over them.
If they show pink you are in ketosis, darker does not mean better, it normally means you are dehydrating yourself!
You may want to start up a journal in the bootcamp/journal forums to help keep track of daily food consumption, excersize, how you are feeling etc. Our Mentors cruise through the journals on a daily basis, ready to assist if they see a problem or to just say what a great job you are doing. Just ask if you need help.