The Linux Foundation finally open their HTTPS certificate service for everyone to join. I am hoping that PortableApps in the future support HTTPS.
I recommend using the Linux Foundation HTTPS. It’s free, automated, and open, for more detail see the website; https://letsencrypt.org/
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The certificate is the easiest and least expensive part:
https://portableapps.com/node/42336#comment-225901
It's also worth noting that none of the 3rd party download hosting and CDNs can make use of Let's Encrypt, so they'd require traditional paid certificates for each one.
Sometimes, the impossible can become possible, if you're awesome!