Getting a WordPress theme is hard

I have been struggling for the last couple of days with getting a new WordPress theme installed on my site.

The main issue I always bump into is that it is really difficult to find someone who can adjust my design wishes to facts on the ground.

For example, I would like to show a description for each category as text. The issues are:

• Should be this done by coding it with PHP on category page?
• Should I pick a theme framework where this is a feature (such as Genesis)?
• Should I try to find a plugin that does this for me?

If I use custom PHP, what happens with an update? If I use a theme framework, does it allow it for me to adjust it the way I want? If I use a plugin, does / will it have security holes in the future and will it be kept up to date?

Also, don’t even get me started on trying to find a designer for the theme with a good grasp on typography.