I think I want to use MultiSite. Let me tell you what I'm doing, and maybe some folks here with more experience than I have (that's like ALL of you) can give me some advice.
I'm a geek. I used to self-host all of my websites on in-house Linux servers. About 6 months ago I moved them "out to the cloud" to a shared hosting site. This has not met my needs or my standards, and I'm contemplating moving them to an unmanaged VPS service like Linode (I actually already manage a mailman mailing list server on Linode, so I'm familiar with it, but certainly other recommendations are welcome). I want to do this "right" though, so I have some questions about MultiSite and even perhaps ProSites.
I current have a membership site (using the Membership plugin here) at http://www.caledonia.net. I also have three other business sites of my own (mostly just blog/lead capture stuff), the makings of 15 other membership sites, three family sites, and I host a website for a customer. The customer has a mostly simple WordPress site.
My thought is, if I used MultiSite and even ProSites, I could allow not only the various people involved in these sites to "manage" their own, but if another small customer pops up wanting hosting, ProSites would make it all flow together well.
Is this a reasonable thought? Where would this possibly "fall apart"? I assume that MultiSite would not be suitable if any of these sites needs their own IP address? But maybe that's not true.
Also, I've become pretty good at "moving" databases for WordPress, but since Multisite uses the same DB, I suspect that I'll have some hacking of the SQL exports to be able to import it all. Any suggestions there welcomed as well!
Any suggestions/feedback here on whether I should go MultiSite or just keep things separate?