To whom do I address the entries? Certainly I write things like "What should I do, Dr. Nbook?" and "Sometimes I just sit with you, Dr. Nbook". These would make one think that I am addressing my writing to Dr. Nbook. This would make perfect sense; after all, nobody else sees the full contents of my writing.
Others could argue that I'm addressing an ordinary reader, someone who will stumble upon this vat of journals after I'm gone. [Let's be realistic. Assuming I live the average lifespan, and assuming that I keep paper journals until then at the rate I'm going now, I really will have a vat, especially after considering that I'm writing in #55 now, and I've been writing since 1998.] Ideally, they would be read in order, but that's not absolutely necessary, as some of the entries are reflective--on the past, on my personality, on my future, on the world around me. If they were to be read at all, though, the reader would probably grow extremely tired of reading them after, say, ten. While Future Reader could learn a lot about me by reading them, what else is to be gained?
Unless I'm addressing them to myself. There's no use in addressing them to Present Me, though, as Present Me is too busy analyzing the past and the future to understand the present. However, Future Me can take a careful look at the events of the now-present and see some common strings, just as one can use a Pensieve to do so in the Potterverse.
Yes, I believe this is the case. While writing is a passion of mine, the true addressee of Dr. Nbook is Future Me, who can use the messages and meanings of what I write now to the fullest. Will she use it, though?
We'll have to wait and see.