Our troop encourages new crossovers to hold off on purchasing new tents right away. (We do have several troop tents available for the boys to use, so that mitigates the problem of someone not having one to use on a campout.) Often the older scouts have suggestions for what works best, and it's good for the new scouts to see several types "in action" before spending money on a good tent. I can say personally that even though our son did wait, he still ended up wanting a different tent a year or so later.
One thing that he loves is his camping mattress. We got this one from REI:
http://www.rei.com/product/778152/rei-camp-bed-35-self-inflating-pad and it's been great. Can't take it backpacking because it's a little on the heavy side, but when they can take the troop trailer into the site it's fine. Even though summer camps always have cots, he usually uses this on top of what's there, and when he'd cold-weather camping it provides much needed insulation from the cold ground.