This is a great idea and something we are working on, stay tuned
Thanks for the input, by this do you mean using Microsoft Rewards points or something different?
This would be a great way to send money for sure although we have something similar that I think you might find some value in called Skype Money. You can find out more about it here:
The other Microsoft account user can login to Skype and you can send money there. Is this similar to what you had in mind?
One option here is to use your Skype Rewards to buy some Credit through the Microsoft Rewards 'Redeem' section:
Thanks for your input. This is possible today, check out this article which explains all of the different ways you can pay for Skype products:
If you used Skype Credit for the first purchase and returned for another, we would show this as the suggested method. But you can always user another by clicking the "Use a new payment method" link on that page.
If you need more specific help, just reply here and I can get in touch with you to help.