Email Questions

[buckeye]

I use Eudora do download email and it has an option for secure SSL connections (STARTTLS - whatever that is?). Would I be able to use this if I purchased a private SSL certificate?

Do you provide a means to check webmail securely through https, or would I need a private certificate for this. My site is just a personal site, in which I don't sell anything, so the only reason I would need a secure connection is for email. I have had my email passwords "stolen" a few times and I now change my password about every 2 weeks just to be safe.

I will be signing up with Hostgator in about 1 month - I paid for 1 year with my current host, which is horrible, and the period end in middle August.