Problems Choosing a Wordpress Theme that works with WP 2.5

I am working on a some new sites and want to go from static pages to Wordpress if I build from scratch. I am sure that some of the other members are looking at a lot of themes too and wonder what to do.

Problem 1: I am a content person, not a programmer but able to "hack" html on some things.
Problem 2: The template on a blog on on one of my sites in a /directory/ is having problems with the upgrade to Wordpress 2.5...the sidebars are currently missing on the "single" post so I don't know what to trust with a different/new template as the creator of that template doesn't seem to answer questions on his blog.
Problem 3: Trusting that any of the templates that are created will work with Wordpress 2.5 and if they do will be kept up by the creator as Wordpress upgrades to 2.6 and will the creator of the theme be available to you down the road if you have problems.
Unless it is a brand new WP template (posted in the last 2 months or has a post about an upgrade, I am finding there are a ton of OLD Wordpress template that don't work with Wordpress 2.5
Problem 4: Finding a Template that will do what I want and that is easily hacked in the css sheet if I have good instructions from the creator, will allow me to add affiliate links
Problem 5: Seeing a lot of templates out there that I like but the color is wrong and most of the sidebars (I want a 3 column) are on the right of the copy and google wants to spider links on the left so your nav should be on the left.

I am looking at some magazine style templates. I really don't want to spend money if there is one that is superior that I can customize without hiring someone.

Thanks to everyone for their input!