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tip: you can use df -h to get that output in "human readable" format, like this:
It is generally a safe option to delete the files in that partition except your current OS version, I have done this with success in the past. If you can, leave the versions before and after your current OS version as well. If you want, you can post the output of ls -al inside /boot, as well as uname -r and I can tell you which files are probably safe to delete so you can update.
I would really recommend NFO change the size of /boot on VM images. I ran into these problems with my VDS too.
200 MB is plenty of space for /boot, but the OS didn't clean it out properly in this case following many updates, most likely. I will work on updating the images.
