I suggest either using pocketmail or handwriting your journal and sending it to a transcriber. You simply won’t have the time to type it yourself when you get to town. Town time is important for relaxing, eating, resupplying, eating, showering, eating, doing laundry, and eating. I would think that your journal would become a low priority and you would eventually stop posting it. Also, computer time at libraries is limited, usually either 30-60 minutes, and that’s not enough time to enter 5 days’ journals.
I’ve kept 4 online journals and used 3 different transcribers, none of whom I have ever met in person. They all volunteered on the site, and I was lucky to always find transcribers who kept my journal up to date. You have to remember that transcribers have lives, too, and they will go on vacation, have work/family crises, etc. There will be times when your journal is not the most important thing in their life.
If you handwrite and mail your journal to a transcriber, you run the risk of losing an envelope in the mail. This has only happened to me once in 4 thru-hikes. If you use pocketmail, you run the risk of having something happen to your device, and you would lose what you’d entered. I’d suggest sending the pocketmail journal to two different email addresses, just in case something happens to the first one.
Two common threads that most journalists live by is to NOT write about trail romances, and to NOT mention other hikers by name/trailname when writing negatively about that person. These online journals are very popular, and you don’t want to hurt someone because of what you wrote.
There will be nights when you don’t feel like writing. When that happens to me, I write a few notes about what happened that day, so that when I eventually write about that day, I’ll remember what happened. Be honest in your journal. If the day sucked, write that. If your blisters hurt, write about that. There will be way more good things than bad things, but I think it’s important to write about everything. When you get home, and it’s December, you’ll enjoy reading about everything that happened to you on the trail.
Good luck with your journal, and have a good hike!
yogi