Hello Kyle,
My name is Ivan Vujisic and I work with Asterisk for 10 years, you can check my freelancer profile at https://www.freelancer.com/u/ivan381eu.html
Speaking of Asterisk extensions realtime status, there is an Asterisk module that put registered peers into the mysql table, but, in my experience, it often fails to remove extension from database table.
Anyway, I can do such installation for you, then write you complete docs so you can reproduce on another server, but we can talk about additional Linux server script I can make for you in order to improve above mentioned (this is not included in price bid).
Please contact me here so we can talk.
Best Regards,
Ivan Vujisic (ivan381eu)