You lasted until Windows 7? I’m guessing you didn’t have to deal with Windows Vista’s bs then. I changed ship thanks to Vista.
I also suffered Windows Me, but I was too young and at that time I didn’t know there was an alternative.
I dual booted Vista/7 and Ubuntu/Mint for a while but after not using Windows in years ended removing it completely. Now I’m a happy Antergos Arch user ¯\_(ツ)_/¯
Self hosting doesn’t mean you should host everything yourself at home, using a VPS you manage (so the data inside it is still yours) is also a viable option for selfhosting. I myself host some services at home and a few others in a VPS.
As for Dyndns, I’ve used a few providers over the years. DuckDNS is the one I’ve been using for 5 years or so and it’s not failed me once. Pretty happy with it.
Maybe you could have a duckdns pointing to your dynamic IP and your domains / subdomains with a CNAME pointing to the dyndns address?