A few questions that need some answers;

1) What kind of an SSL would I need to be able to do the following:
- Have cPanel and WHM log in via SSL
- Have WHMAutoPilot use SSL

Can I do this with one SSL cert.?

As well, what are some SSL cert. distributors that accept PayPal.

You should be able to do them all via 1 cert, as long as they all use the same domain.

If they dont use the same domain, then you need either separate certs, or a wildcard cert (~$500/year)

You can get SSL Certs for $49/year at www.instantssl.com

Or click 'SSL Certificates' on the lil menu bar right under the banner :)

Any sites that issue SSL Certs. that are payable via PayPal?

You don't need PayPal. Apply for the PayPal Visa and once you get it you can use that for credit card payments. ;)

True :)
Howerver, I'm underage and the PayPal is under my moms name. I don't feel like bugging her to use her CC again, already ordered a server and PerlDesk.

Well...you might be able to find someone who's a Comodo reseller that accepts PayPal.

I would say you should get a chained SSL cert which you can get from EV1 servers for about $20 a year.

You can still generate a self-signed certificate that costs nothing .. exept that user will see an alert each time they connected to ssl site.

ChainedSSL works well for what you are trying to do. I installed it and everything works great. :D

We ordered a CompletePro SSL Cert.
http://www.completessl.com/completepro_ssl.php

Do you think it'll do what we want?

yeah, sure. So long as you ordered it for servername.domain.com