Virtualhost file for Multisite?

Is that your entire file? You don’t have any directives for handling HTTPS. i.e. <VirtualHost *:443> blocks. But before doing HTTPS, be sure the regular *:80 directives are correctly working. For now, comment out (line starts with #) the rewrite to HTTPS part until you are sure the *:80 directives work.

Remember to restart Apache after making changes.

What behavior do you want for each domain (boosterclubnetwork.com and madisonboosters.com)? Right now they both go to the same place. (the DocumentRoot directive) There could be other downstream directives altering the final destinations.

What multisite setup are you using? subdirectory or subdomain? For complete domain redirects in virtual host, subdirectory is preferable. What folder is your multisite installed in?

ServerName directive should not include transport protocol (http://)

I’d also comment out the <directory> blocks for now. You don’t need permissions confusing the issue right now. You can restore them for testing once the basic configuration is working correctly.

Yes, SSL would complicate things. Focus on simple HTTP requests first, even if you intend to rewrite all to HTTPS. Disclaimer: I’ve not setup both subdomains and multiple domains for a single multisite installation before. With a multisite subdomain configuration, I think you would be forced to rewrite alternate domains to the subdomain.main_domain equivalent for WP to recognize the request. This cannot be done internally, meaning the new address will show in the address bar. Internal rewrites would not show in the address bar.

I think it would be better to use a subdirectory based multisite and manually (via virtual host and .htaccess directives) handle the various subdomain and alternate domain requests, sending them to the correct subdirectory. These rewrites can be handled internally so the original request remains in the address bar. The drawback is you could not add additional subdomains on the fly because they have to be coded as a rewrite directive. You could still add subdirectory sites on the fly.

You cannot have wildcard subdomains with LetsEncrypt certificates anyway, so the loss of on the fly subdomain site creation by going to subdirectory configuration shouldn’t be much of a loss. Even though Apache will not alter the address bar with internal rewrites, WP will still redirect to whatever URL it is configured to use in the options table. To have WP also maintain the original request, the WP_SITEURL and WP_HOME constants should be dynamically defined as demonstrated in the Codex.

Once you have the rewrites working the way you want with HTTP requests, duplicate your <VirtualHost *:80> blocks and change the 80 to 443 in the copies to handle HTTPS requests. In the 443 versions, add in the SSL directives that point to your certificate files.

Once HTTPS requests are also handled correctly, you can finally add the HTTP to HTTPS rewrite directives in the *:80 blocks.