Yikes! It's always such a pain to install ISA on a web server.... Best scenario is to have a separate web server from your ISA server, and I use server publishing.. I don't use reverse proxy "Web publishing" and it works like a champ.
If you just can't do that.... and it all must be on one server, www.isaserver.org is your friend.
However, you can definitely configure DNN to accept whatever port you'd like, and each site can accept multiple names/ports as well.
Admin > Site Setting > Scroll to bottom of page.
Add new http alias: www.mydomain.com:8000
So now you might have a couple listed here.
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