I still to this day dream of when I can justify a Honda Pioneer or a Can Am Commander, the two I like best. I have looked at a lot of the Pioneers and some of them have a ridiculous amount of bells and whistles that just drive the price up even worse, I'm sure others are that way as well.
As stated above identify what you NEED, build from there, look at as many types as possible. I am a Honda fan for the most part and have always had good luck with their ATV's, I like their fold up seat options, feel comfortable, good box space, good reliability ratings, drove a 700 with tracks (no power steering) and liked the way it handled and the soft cab was ok on it.
Just another thought would be a 4 wheeler with a box, Artic Cat has one that looks good and have used a Ranger with one that was handy and comfortable, but the prices on them start creeping to SXS.
Good luck.