Anonymity and ...
OK, so, here goes the rule for recognizing journals.
Yes, if you had reasonable encounters with an individual, you could recognize the handwriting. We're making this far easier than it would in RL, but not an all encompassing thing. So, Sirius would not be able to recognize Blaise's handwriting. However, Blaise and Ginny were Slug Club together.
HOWEVER, if you want anonymity, dictoquills and anonymity charms are good. And yes, you can do pen names and have fun with that.
For example, Draco writes a dicto-quilled, anonymous entry and signs it "Star Boy" (he's threatening to kill me currently for this), then people would only know that "Star Boy" wrote it.
Eventually, someone COULD come up with the understanding that "Star Boy" is Draco, and then he would kill me in my sleep ;-)
Does that make sense to everyone?
Also, please mind your tags. If you need one, let us know. ;-) Luvs - The Mods