1) Order a clean server with Plesk 8 installed already. sw-soft really screwed up the upgrade process, and you'll find you will end up with more headaches than are worth it. Either go clean, or stick with 7.5.4, which you know works.
2) The easiest is not always the best. The web-based updater will work, sometimes. There are a lot of problems people are discovering in the update that you would have to hunt through server logs in order to fix. The best way is to download the ~1.5mb autoinstaller from the sw-soft downloads page, and run it from SSH. This will let you observe the process as it happens, and know right away of any problems it runs into.
3) Other than whether the server will still serve webpages without some tweaking and reupdating? Nothing more than usual. If you update, you run the risk of some pretty hefty server loads, and your server no longer delivering mail to root (logwatch files, and Plesk cron notices, for example). drweb is causing quite a number of headaches, as is the communications between spamassassin and qmail slowing to a crawl, and shooting the resource usage through the roof. Those who start clean with 8.0 are finding this less. Oh yeah... the backup process is **** now, and the files you generate with 7.5.4 are VERY likely not going to be readable with 8.0 (there are a few people who say that they are, but a search of the forum will show many more saying they are not).
4) No. You will want to use a program like yum to update your php and mysql manually. atomicrocketturtle has a repository that can handle this for you.
I am really pushing on you here to either stick with 7.5.4 until sw-soft figures out how to release patches, or migrate to a clean Plesk 8. A search of Plesk 8 problems on any number of support boards or Google will only further support this suggestion.
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