I use a Chicago Pneumatic at work almost daily, really like it. It's much better than HF version... As far req'd CFM cp should have specs on their website, just remeber to oil frequently.
I have both hex t handles and long sockets. Both have their place but I reach for the t handles first if I have the room. I have Eklind Bondhus and Whia at work and each one will serve you well and are all quite affordable.
Anothor option would be something like the Williams ratchting t handle...
To add, those are half ball small hole gages. They can get into shallow bores, they also make full ball ones which I kinda perfer. And Helios is a german manufactuer pretty decent stuff.
Looks like you have you have some step dowels or diamond dressers in there, along with some small boring bars. Step dowels are used to go from one nominal size dowel to the next, used when you need to hand align parts (die block and a punch for example) or when you screw up and put the dowel in...
The red handled tool is a dresser for grinding wheels, pedestal grinders to be exact. Hard to tell what the other stuff is. Can you get some close up pics?