Airlines vary on how many buddy passes (un-buddy passes ) employees get in a year. I think after your first experience with the buddy pass you may not want to use one again. There is a saying among airline folks "friends don't give friends buddy passes" When I was at the airlines, I never gave them out to close friends. I did once, and my friend bombarded me with phone calls and text messages on the process and why he wasn't getting a seat and if there was anything I can do to help him. When I wasn't able to assist him, he became agitated and at times, hostile. Fortunately we worked through it but it was a valuable lesson.

Expect an extended delay at the airport and have a solid plan B,C and D. Again, it really depends where and when you are planning to travel. Once you figure out what days you want to go, I would ask your friend to check on the loads for that day. It will, at least give you an idea on your odds of getting a seat. Check the loads a week prior to when you want to go. I wouldnt attempt anything with under 25 seats available.
Its important to know, you are at the bottom of the standby list. A buddy pass is the lowest priority and if you do get on and someone shows up to the gate at the last minute with some sory of priority, you're getting the boot. I would also stay far away from anything with a connection. Good luck