I have the original version (1.0 I think) and seriously considering upgrading. It makes updating large sites so much easier. I'm currently using Wordpress to build my sites due to the plugins that's available, but the ease of updating is very similar. However, due to the rise in popularity and effectiveness in designing a "silo" type of website I've seriously considered using the upgraded version of xsitepro. You can build silo type of sites in Wordpress, but xsitepro sites would look cleaner and in my opnion would be easier to build, plus it's more flexible. Not as flexible as HTML/CSS sites unless you "tweak" it a bit though. JMO
Actually, I signed up as an affiliate as well, probably should put that link in my sig. but anyway I really like it so far
Yeah it's A LOT faster than trying to build large sites from HTML, it automatically updates the changes you make on all your pages. I heard the templates in this version is better, along with the coding and feeds. Several years ago I built several sites then put it on the side and got involved with Wordpress (because of the feeds, pinging, rss, plugins, etc.), maybe it's time to take a look at the new version.
I played around with XSitePro2 and found it pretty easy to create a quick and dirty 'silo' site and the large # of templates with graphics is nice. However, it creates horrible code, and there is no way (I found) to use and edit a CSS stylesheet. As for Wordpress, I've considered using it for my sites that are mainly HTML, but I keep coming back to the fact that WP is a database driven, dynamic content application. Even with caching plugins, WP is still going to take up more resources than a straight static HTML site. It is also something that you need to keep a closer eye on - for example, in the event of security updates, etc. That's just more of a time requirement to maintain. I'm now at the point of trialing Dreamweaver. I just launched it and I already like it better than anything else I've tried so far. Of course, it's at least double the cost of XSitePro2, but hey, this may be a case where you get what you pay for!