separate WordPress sites vs using multisite feature of WP3.0

Question

I will be using WordPress 3.0 to build numerous sites, roughly 300+. these sites have the following qualities

1. content may or may not be related to each other.
2. Each have the same set of admin users - a person who has an admin account in website A has the same account in website B.
3. each are top level domains. no subdomains.
4. each site needs to be debugged in isolation ( it would be a mess to look at log files for all 300+ sites)
5. The sites will run in IIS ( Not sure if this matters )

I have never used or setup the multisite feature before.

Is it better to have separate WordPress sites or to use version 3.0's multisite feature? I was going to use separate WordPress sites because I was afraid that the multisite feature setup might be a nightmare with IIS.

Thanks in advance.

Answer 1

I don't use IIS, so I can't really say anything to how well it handles Multisite, but I do know that multisite was tested to run in IIS. Presumably, it can handle that many sites as well.

One consideration that I think is worth pointing out is the authentication question. If you have an admin who needs to make a change network-wide (deactivating or activating a plugin, for example), not only will that task need to be done 300 times, but that admin will have to log in 300 times too, since non networked sites don't share cookies. With multisite, that will only need to happen once.

My suggestion is this: try doing it on a test environment and see if you think Multisite is worth it for you. If it works out, go for it, because it will end up saving you a lot of time.

Answer 2

Yes, the domain mapping plugin is required and also requires some .htaccess (Apache--not IIS) directives in order to work. So this might be a "no-go".