Dye my hair?

I always have this idea in my head that I should dye my hair.  The problem is I never do it.  I fleetingly think that I should do something to make my hair colour more vibrant and rich.  But what?  Do I go Georgina blond (don't think that I could pull it off), Breanna dark brown (really don't know what that would do for my complexion), or Katie highlights (nice but seem high maintenance).  I know that I should probably do something that is my own.  But what?  I have never hopped on that train.  But I am feeling the winter blues and think that this will make me feel better.  Here's the thing.  I think that I am way to cheap to pay to have a professional do it.  So, do I dye it out of a box?  Which I have do before and have only had one major mishap in college.  Or pay someone....

I have had people comment on my "chocolate brown" hair before saying they love the colour.  But, it has been this colour for most of my life.  I need a change.  And really how many 27 year-olds do you know that don't dye there hair.  Decisions, decisions...