I have an iPod touch (3rd generation) with a little over $200 worth of apps and content that I've paid for.
Apps can be re-downloaded if they're deleted at no additional charge from iTunes, however you'd need to do this one by one. They should be on your computer anyway, so it would just be a case of re-syncing.
Music is your responsibility, you can't redownload it for free, it should be on your computer anyway.
I am wanting to jailbreak my iPod (preferably with redsn0w, iLiberty+, or jailbreakme.com) but I am cautious because I am unaware if I will lose any functionality, applications, or data that already exist on my device.
What firmware is your device on? (Settings > General > About > Version)
Depending on the firmware, you may have to restore your iPod in iTunes, so it will be wiped of all data. As I said you can just re-eync afterwards. If you do a 'backup' in iTunes first, all your settings and app data will be backed up too so it can be restored after 'restoring' the iPod in iTunes. However, backups might not stick sometimes, so be aware that you might lose your app data.
You will not lose any functionality, except maybe game centre... (?)
Will my device be at risk of bricking? Will I have to rejailbreak often?
You can't brick your device.
Every time you update your device you will lose the jailbreak, so you'd have to wait for a new jailbreak to be released for the latest firmware to be jailbroken before you could jailbreak it again, if you updated.