it all depends on Disk usage and how much you rely on fast seek/load times.
If your OS is on SSD and you don't need fast seek/load times on HDD, once/week/month is fine.
The more free space you have, the less often you generally need to defragment the disk since most of files will be stored on the free space which means most of them are not fragmented from the start. This does not apply if free space is created by constantly deleting files, since that leaves holes which are filled first and thus new writes are fragmented.
Fragmented hard drive doesn't break, it just gradually gets slower and slower since every file is spread around the hard disk platter and are not in one part.
Yes, windows 7+ does it automatically in background as part of normal upkeep.
Yes, while microsoft licensed diskeeper for their defragmentation tools for windows, they never wanted to pay much. as such they are lacking "do it when you wont notice it" and intelliwrite part ("do it before it's written to disk")
Both of which in my opinion are quite nice, thus I pay for it and.. never bother about doing it since I don't need to.