as far as used midsizes go my dad has an 09 dakota quad cab w/ almost 150k on it, 0 problems other than maintance, great little truck with a v8 (if you want that your stuck with the dodge IIRC), however they dont make them new right now, rumor has it a jeep wrangler pickup will be coming out in the next year or so to fill that slot in the Chrysler motors lineup. If it were me id be looking for 10 or 11 dakota (They changed the front end in 08) with a v8 and 4 doors, 4x4 and tow package. If you have any specific questions about the dakotas let me know i have spent enough time driving it i can probably answer for you.
that said, the bed IS short, my road bike just barely fits in with the tailgate closed, and none of my mountain bikes fit with the tonneau cover on it, and my full size RAM 1500 gets better gas milage with the HEMI. the midsizes dont actually save you anything on gas and you give up ALOT for the little bit of flexibility/maneuverability in parking lots.
that said, the bed IS short, my road bike just barely fits in with the tailgate closed, and none of my mountain bikes fit with the tonneau cover on it, and my full size RAM 1500 gets better gas milage with the HEMI. the midsizes dont actually save you anything on gas and you give up ALOT for the little bit of flexibility/maneuverability in parking lots.