Glad to see you already found Scheduler
Did you add a task that just repeats itself every night that goes through all users to check their signup date? Because if you did, I do have another idea for you that might be interesting based on what we have set up on modmore.com..
Rather than looping over all users, we have a task signup_reminder_14d that we schedule in a hook during the signup. When calling $task->schedule() we pass it the second param with the user ID, like so:
$task->schedule('+14 days', array('user' => $userId));
In the signup_reminder_14d task we then grab that users' email and send him a reminder if necessary.
This way we can see via the scheduler component what exactly happened or is going to happen, and users also get the notification at roughly the same time they signed up, rather than in the middle of the night. Approaching it like that makes it more like a message queue rather than just an interface for cron jobs, so I just wanted to give that perspective