While this may be an obstacle for you right now, the fact that the scheduled reminders system doesn't send out reminders after the first one is definitely a good thing. If you have the job for sending scheduled reminders set to hourly (my preferred method, since it avoids the possibility that reminders only ever go out late at night, making them unreliable for reminding someone about something tomorrow), you don't want everyone to get a reminder every hour.
If you want to remind someone multiple times per activity, you have two options:
- If you want the same message to go out, and the interval should be the same (every couple of days or something), enable repetition.
- If you want to vary the message or have a custom schedule (one month out, one week out, and then one day before, for example), just set up multiple reminders. The system limits the reminders to once per reminder so other reminders set for the same activity won't interfere with each other.