The first time I dealt with WordPress was when I first started doing IT administration for FanHistory. At that point in time I knew nothing about it and it was breaking horribly. Luckily I managed to fix the issues (which turned out to be Varnish proxy related) and get it standing mostly on its own two feet. One of “minor annoyances” I ran into then and absolutely had to figure out during my migration, was the lack of SSH or SFTP based updates. By default when you go into add or update the plugins (or the software itself) you have only two options FTP and FTPS (SSL). I run neither of these, FTP is majorly old and very insecure. FTPS is just not common. I thought I was stuck doing things manually, until I found out…. You can enable SSH2 based updates in WordPress. Better yet, it is SUPER easy.