Documentation for multiple, independent sites

I’m looking at options of moving 4 ACF sites to Lucee site. Currently they are all on the same Windows server running Apache (I know, it’s an odd setup but I digress).

The folks over at Hostek have a really good price on a Lucee VPS but before I move the sites, I have a couple of questions:

Under Apache, I simply direct the URL to the folder containing the code base for that site. I assume I’ll do the same sort of setup with IIS, correct?

I’m also assuming I can do this locally as well ahead of time to test before I purchase the VPS, right? It’s been years since I’ve done a migration and the last one I did was like for like. This will be a server upgrade, CF upgrade, and a web server change. What can go wrong? (rhetorical).