’”I’ve been through this process myself long before there were the handy tools and improved import features in WordPress, so I understand where you are coming from. As for creating a static front page, create a “Pageâ€? in WordPress and assign that as the front page. Personally, with a good Theme where you can easily customize the front page, I don’t see any reason to bother with a static front page in the old sense, as I want a dynamic front page portal to my site. It’s so much more user friendly and better SEO.

As for the drop in page rank, don’t worry. With your site in WordPress and out of static, your pings will increase and that page rank 4 you fought for should actually go much higher as WordPress is so SEO friendly. Years ago, we had to wait months and months for any recovery in ranking from changes, even changing domains or web hosts with no change in the domain.

Using a sitemap Plugin will help those redirects and indexing, too.

However, the Plugin you mention I recommend I don’t recommend for new versions of WordPress, and I hope you are using the latest version as past versions have security vulnerabilities and bugs. The latest version of WordPress has built-in image loading through the Gallery feature. Give it a try. It’s wonderful. However, it does change the URL structure for your images. I recommend that if you are not moving your site around, you make sure your images stay in their folders on your server and the links to them be absolute, and you should have no problems at all with them. And nothing to upload.

I haven’t written about this subject in a while, so you’ve reminded me that it is probably past due. “Thanks for the kick in the butt and good luck with the changes. I think you are going to be so much happier. Heck, I KNOW you will be much happier.

Having done this too many times, here are some clarifications.

1. Google isn’t the only player in town. On a WordPress blog, you will actually automatically improve your SEO value across ALL search engines over a very short period of time, so don’t worry too much over the redircts issue. It is MORE important that your users have a seamless experience. A good XML sitemap will help search engines, too, as you mentioned.

2. If your images are absolute links not relative, then just FTP upload your images into their original directories that match the link URL structure and you don’t have to mess with them later. WordPress has a funky way of storing images that I’m not a fan of, linked to the post by date. Learn to live with the structure of uploading new images, but keep all your old images where ever they were and you don’t have to deal with URL changes for images. That saved me a ton of time.

3. The “quirk” in the home page issue is a Theme issue, not WordPress, though they are considering how to deal with this as it comes up repeatedly. The template tag used to generate the listing of your Pages, including “home” (the root index page) doesn’t check the “home” page setting. Dig into the template file and manually set the “home” link to whatever you want, and then let the tag take care of the rest, excluding that link. Check the WordPress Codex for specifics on how to do that. I’ve done that for years with great success.

4. About the installation to the root, that is the smartest choice. You do not want your URL to have the word “blog” or “wordpress” or another variation as that becomes a keyword, diluting your keyword mix, and making your URL longer than it needs to be. I always recommend installation to the root directory. Much cleaner.

Your last three points (7, 8, and 9) don’t really have much to do with converting from a static site. Upgrading is part of the process of everything, static or not. I had to upgrade static sites all the time for various reasons, including changes in scripts and code. Natural part of the process. Luckily, WordPress is working hard on making the process of handling upgrades even easier.

The same applies to security issues. When they are found, you deal with them, no different than anything else. If you keep WordPress upgraded and you monitor WordPress news for updates, not a problem. WordPress is more response than most to these issues.

The Duplicate Content issue was exaggerated. Static content sites can also have duplicate content issues. The point is that this is easily resolved if you have worries about it with a well-designed Theme. By using excerpts on multi-post pageviews, much of the problem is automatically solved.

Good work. Too many people are afraid to convert to dynamic content generation platforms. It is life changing, and I can’t recommend it enough. If I can survive a 2,000+ static web page to dynamic (WordPress) conversion, so can others.