Honestly I love all of my gear. I really enjoy camping and sports gear for its practical and esthetic qualities. I went through years of research and experimentation, buying things and reselling them on Craigslist when I found something better. Over the years you learn more, you become more committed to your favorite activities, and they come out with new things you have to try. I put together different sets of gear for different uses (car camping, kayak camping, backpacking). Current favorites:
TENT: Kelty Trailridge 2, 3, and 4
MATTRESSES: 3 different Expeds + REI Campbed 3.5
SLEEPING BAGS: LL BEAN down 20 and 35 degrees
COTS: Camptime Roll-a-Cot and Helinox Cot One
CHAIR: Helinox Sunset chair + favorite old webbed lawn chair
KAYAK: Hurricane Sojourn 135. Can camp with it for a week.
CAR: Scion xA. Yup, I'm serious. Perfect tiny adventure car for one person. Holds kayak, bike, and camping equipment.
One thing I haven't found yet: a miniature camp kitchen, like 1/3 the size of Mr. Leary's.