You're running into a limitation with either iOS or perhaps Xcode. There's a way around, as I'll explain.
What you see it the console view (within Xcode's organizer window) comes from the Apple System Logger (ASL for short). However, as you noticed this log seems rather short. This is either because iOS itself keeps it's logging database very small, or Xcode only fetches and displays a very limited history.
Quick side note:
What does NSLog do? It does two things. First it sends your log message to the Apple System Logger. This is essentially a daemon process that takes log entries and writes them to a system database. But, this doesn't actually display anything on screen. So then NSLog does the usual writing to stderr (aka the TTY). And it's this step that causes it to be written to screen, where it appears in the Xcode console.
With Lumberjack, things are a bit more flexible and transparent. Try disabling the TTY logger in your setup, but keep the ASL logger. You'll notice you still see your log statements in the console view via Xcode's organizer. But you won't see anything in Xcode's console while debugging. Now try the reverse. Enable TTY, but disable ASL. Now you'll see output while debugging in Xcode. But your logs will be absent from system log in organizer.
Long story short, there's no easy way around the ASL limitation imposed by Apple. So instead, just use a file logger. You have complete control over your logging history this way. And whenever you need, you can just grab the log files from the device or simulator and inspect them.
Let me know if this helps.