Well, in real life, the most plausible situation would be that Person 1 picks a well-known disk encryption application, which encrypts things based on a password (which he picks based on his experience in school).
Person 2 guesses the application (or the application leaves some fingerprints on the disk, for example, a cleartext application that allows you to enter the password and 'unlock' the disk), and then guesses the password (based on their shared experience).
Of course, this isn't a very sexy (or sophisticated) scenario - just the most realistic. If you were looking for something that would give you an excuse for Person 2 to dive into cryptography, this isn't it.
Whether this works for you (as an author) would depend on what you want the reader to get out of this (e.g. that Person 2 is really quite technically adept, for example)
And, to answer your questions (at least for this scenario):
- What process should Person 2 follow to figure out the encryption model used in the drive?
Really up to you - these possibilities are all plausible:
- having person 2 know enough about person 1 that they're likely to use a specific application (e.g. they're a MicroSquirt(tm) fan boy and so likely to use MicroSquirt's disk encryptor)
- just guessing it (and maybe having to go through several possibilities)
- seeing evidence on the disk
- What flaw in the encryption would allow Person 2 to decrypt the drive - the flaw could be generated by Person 1's impatience to get the task done.
In this scenario, choosing an easily guessable password (to make it memorable; a password such as qasQ-zD-1zu3iL2b6kAtGYMwSR/uZMyy/Apn$A1s
is secure, but not very memorable; a password such as GoOrangeAndBlue
is memorable, but perhaps not as secure to someone who went to that school).
- How long do you think the decryption process would take, and what equipment would Person 2 need to have to perform the task? Assume limited resources, so no quantum computer available.
Again, up to you. It may be that person 2 would need to go through billions of potential passwords to find the right one (and so would need some nontrivial amount of equipment), or he might guess it at the first couple of tries.
- How long would it take for Person 1 to encrypt such a drive, and what equipment would he need to get that task done? Again, no quantum computer allowed.
Not long at all - the task really is limited by how fast you can read/write the drive...