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I think it could depend upon your long-term plan for these pages. If it's all original, useful content as you say, then I can't see any negative effects of launching it all at once. The problem could come more in how you plan on promoting these pages and how many of these pages are going to be important pages within your website. If there are key pages, depending upon the team and resources that you have to promote these pages, you might consider releasing them over time so you don't have a glut of content sitting there without promotion in social media/PR/link building efforts because you don't have enough people-power, time, or money to get the word out about it all.

On the other hand, if your plan is just passive, receiving long-tail search traffic as the search engines work their way through all of that content, then why delay?

It's just such a headache updating Wordpress across multiple sites all the time! Do you really think that the separate IP addresses bring much benefit? I can do that too, but just didn't know if the added expense would really pay any dividends. I wonder if you could still set up separate IPs if you set up multisite?

I manage multiple websites in Wordpress and the idea of managing them all under one Wordpress install is very attractive. Are there any dangers SEO-wise to doing so? I know that all of the sites would live under the same IP address, but that's not something I'm really concerned with anyway because I don't do a lot of inter-linking between the sites. Thanks for your help!

-El Juano

Unfortunately, I don't know of such a tool. It will take some more research on your part to see if other sites using the same server are getting the same treatment from Google. It is curious that Barry Smith was able to find your sites showing up. It's possible that Google's algorithym change has adversely affected your SEO results if you were relying heavily on links from websites that Google depreciated as "content farms".

I would do some Google searches for the primary target keywords for the domain in question. If the site is ranking well, then you can bet that Google likes the site regardless of what the tool bar says.

If indeed your host is to blame for getting the boot from Google, then you need to move your websites ASAP. Applying for reindexing probably isn't going to get you very far if your host is the root of the problem. You might consider upgrading to a virtual private server.