This is (or should be!) a massively interesting topic for theme developers.

As a theme 'user' myself prior to developing them I had similar experiences. I would love a particular theme design, but trying to apply that to my own site involved nothing short of a wrestling match!

Now that I develop themes (with Scott Bolinger) we obviously begin with an initial design concept but we try to focus on user experience too. We are always looking for ways to make it as easier for users to start building out their sites.

Going back to being a theme user, I guess the number one issue I had when using different themes was that every theme seemed to have a different way of doing things! This was confusing to me, and was compounded by my inexperience with WordPress itself at the time. Even though themes had (or promised to have) the features I wanted it could be cryptic to actually get something to work. Only by posting in forums for help could you get the answer you needed.

Also, and this happened again an again, when I activated a theme, it would look a bit naff out of the box, only with a bit of TLC did it resemble anything like the theme demo, or like a site I would dare to show to others.

We have addressed this last problem somewhat in our themes with a new feature we are still experimenting with. When you activate a theme you basically get an option to install some default content for that theme. This has to be optional in case you are activating a theme with existing content. The default content consists of automatic creation of a few pages (sitemap, contact, about, blog), a nav menu (adding pages, and setting the theme location), and populating a widget area with one or two widgets.

There are many other things we could do I'm sure, but hopefully we are on the right track.

How about everyone else? What good/bad experiences have you had as a theme user, and what would have made it easier to get a theme to do what you wanted it to do from initial activation?