Katrina

You can do it. I set mine up ages ago. https://docs.pi-hole.net/guides/dns/cloudflared/

I’m not sure you could even run pihole on 512MB RAM.

And the biggest disadvantage of IPv6 is that each of your internal devices has its own address and can be directly accessible from outside. So you need to completely rethink how you do security.

DNS obviously, I use the Pi-hole compatible filtering in OpnSense Then Nextcloud, Email, Navidrome, Jupyter Hub, Code-Server

Their adverts are all about websites for people who don’t know how to create websites.

Squarespace seems to be targeting a very different market.

I have about 25 letsencrypt certificates on the same domain, so that is definitely not an issue.

Just bear in mind that microsoft.com is hosted on Linux. If Microsoft don’t host their own website on IIS, why would anyone else?