Ive started to acquire quite a bit of sites and it would be hassle to manually backup 50+ sites somewhat regularly. Is there any way to setup a system that backs up the files I need to be able to recoup a site that has (for some reason) gone lost? I am guessing I need to backup databases and themes. Anyway to do this automatically and to get it to upload to dropbox or somewhere I please? Anyone have some tips or links to some guides on how to set something like this up?
If you on shared hosting I would suggest plugins like BackWPup or WordPress Backup to Dropbox. If you have VPS then there are many additional paid and free options (I personaly use rsnapshot and R1soft).
I use UpdraftPlus, which is free. It does scheduled backups of just the database, just the files, or both - or a separate schedule for each type of backup. It also connects to Dropbox automatically and sends the backups there. Very controllable, does email notification and a bunch of other stuff. The down-side is the occasional "reminder" in the admin screens that there's a premium version - though the reminders can be hidden for 12 weeks at a time, so they're not annoying.