I purchased Ascendo Money on Handango a few months ago along with the redownload certificate thing. I'm about to switch phones to another blackberry. Will I be able to redownload the software again but on a different phone???? Do I have to pay for it again??????

Often the license numbers are tied to the PIN of the device, but you will need to as Ascendo if it is.

You can download until your heart's content, generally. Ascendo has a fully functional demo program. What you will need to do is apply the license key again. If you saved your email that contained your key, you can just enter that key in again, after re-installation. Otherwise, I think you may need to contact Handango so they can email you the activation key again.

Edit: What JSanders said.... you may have to contact Handango or Ascendo to have them change the PIN associated with your license

I saw a similar question in another thread (a poster said you have to re-purchase the software if you change device which I didn't believe to be true) so I contacted Ascendo and asked what happens if I get a new device. They replied:
"Most distributors like Handango will allow you to load a new PIN to your profile and generate a new registration key."

I would contact Ascendo or Handango for more guidance they are pretty fast with their response.