I have about 30 (this number will most likely grow over the next few years to 50 or more) unencrypted laptops that I have been tasked to encrypt (entire drive). These machines will be used off site regularly by my users. These machines are running Windows 7 and XP (about 50/50), but more Windows 7 every month. I have experience with Truecrypt, and have had no issues. It appears to be THE solution for a free solution.

My concern with Truecrypt is that my users will have 2 passswords needed to login to their machines. Also, I need to choose to either have 1 password for my organization, or carefully document each machine's password (management nightmare). In my mind, choosing between a managed and a free encryption solution is primarily based on the NUMBER of machines that will be encrypted and supported.

Two questions:

1. From a management standpoint, what is the tipping point of users where a managed solution would pay for itself over Truecrypt?
2. What are some good third party solutions? (I will consider Bitlocker, but the price to upgrade Windows 7 licenses is a turn-off)

I would love to hear from some admins with experience in supporting encrypted machines in a corporate environment.

Many thanks in advance!