Yeah, the roll pin in the first picture can/will come out.
Sure, the spiral pins will/can come out in the second picture, but why would you want them out?
No, there should not be that much play in the collar and bushing, looks to have been wearing on the collar... Looks rather dry also. Did this clutch work when you got the tractor, or haven't you tried it?
There are some parts of the assembly that are no longer available, and you would have to have them built. Jeff in pa builds parts for these tractors.