I currently work in FrontPage 2003 and have over 300 websites which are all static html and manually update. Nothing is dynamic. Each website is for a particular city so one templete could be used for all and then I just need to populate with my content, etc.
Any software recommendations? Needs to be easy to use. Price needs to be under $2,000
With that number of sites, I'd check out Typo3. It has an extension that lets you "spawn" a bunch of sites off of one installation. The learning curve is said to be pretty steep, but the reward is the sheer power you get.
We use WebGUI by Plain Black. It can manage many sites with one install. There's a bit of a learning curve. You could set-up your initial site, then duplicate that. If you're comfortable working with MySQL, you could set-up your one site, layout and structure, sans content, then dump that data and use it to replicate your other sites, ready for content. Each site would have it's own admin.
If you do have $2,000 to spend, I'd recommend hiring someone to write you a custom CMS. That is, if the editing is not extremely advanced. I've worked with several sites using CMSs and I don't like any of them. It never gives you the ability to do exactly what you want.