1. I don't think anything is automatic when moving from DW8 to DW CC2017. You'll likely need to set up your site definitions manually from your local files. However, once your sites are properly defined in the new program, it can synchronize the files the same way it always has.
2. Don't let the "cloud" in Creative Cloud throw you off. It's not "Cloud Based Software". The programs download from Adobe and are installed directly on your computer, just as they were before CC was a thing. While there are a few cloud-based goodies with CC, the bulk of the subscription is simply a download/delivery service.
3. I'm not sure what jargon is throwing you off, if there's something specific, the folks here would be happy to help.
DW CC2017 is quite a bit different from DW8. The basic functionality hasn't changed much, but a lot of the bells and whistles have. There have been quite a few items that have come and gone from the program over the decade plus since DW8 was released. If you depend on those functions, it's going to be difficult to get up and running in the newer version unless you know how to hand code for the options that have been lost.
Setting up a site definition in DWCC2017 hasn't changed much. As long as you have either the local copies of your site files, or FTP access to your hosting server, getting your site into DW is pretty easy: Define a site
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