Schedule Reminder executed but no email sent out
A contact is added to the list of scheduled reminder recipients when they first meets the criteria you have specified and the reminders will be re-sent to that list on your repetition schedule.

If you ran your scheduled reminder for the first time when your membership end date is in 3 days then it won't be on the reminders email list.  Only memberships with end dates 2 weeks in advance will be added to the list.  

You can confirm this is the case by adjusting the end date for your test record to 15 days away then wait for 1 day to see if the reminder is sent. 

Also, although you haven't asked about this, are you sure you want to send 24 reminder emails to your members each day for 15 consecutive days?  That is what will happen with the settings you describe (assuming your cron runs at least hourly). It seems like a perfect way to annoy your members and get  blacklisted for spamming.  

I also suggest you upgrade to 4.4.16 as there have been bug fixes and security updates since 4.4.6  .