Self-hosting is possible, but very hard. Getting DNS and SSL certificates just right both inside your LAN, and while accessing your LAN remotely (through a VPN) is brutally hard. You will almost certainly need to leave Windows behind to achieve this. Windows hates your meticulously-configured local DNS server, which is not one of their (relatively expensive) Active Directory (TM) DNS servers.
If you have someone with strong nerd powers in your extended family, perhaps they can set up something that can benefit the rest of the family, creating a sort of clan-wide "medieval castle" of sorts. And that helpful nerd should be rewarded abundantly with pizza, coffee, and other favors.
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"Life is not a problem to be solved, but a reality to be experienced." - Soren Kierkegaard