For your first question, I have a doubt here is 1W, 2W, 3W, 4W, 1M and so on are TIME BASED activity why are you using measuring point for entering this reading?
Also, I have a question here is what reading are you entering here as measurement document?
System does the calcluation of Time based activities itself I dont think you need to enter the readings in measuring point for the same.
For your second question, for auto release of Maintenance calls you may use the transaction IP30 (manually) or IP30 (Background).
With IP30 Manually you can release the maintenance calls for multiple maintenance plans at one go.
With IP30 Background you may schedule jobs so that System would release the Maintenance plan calls automatically based on your schedule.
Hope I have clarified your doubts.
Please do tell me if you have any further questions related to this.
Chin2.