The 257 Roberts case is about .2" longer than a358, 308, 243, 7mm 08 cases. Not sure if it will fit in your magazine or not with a bullet seated very far out. You may not be able to come close to the lands and still fit the mag. I am fairly sure you could make it a single shot and take them in and out as a single and seat the bullets out to normal OAL. BTW the head size is the same as a 22-250 so that is not a worry. If you decide to change head sizes, like go to a 223 then you can switch heads and voila you have a 223. I am not sure about magazine issues. I have 2 Stevens that I have 5 barrels for. I have converted them both over to single shots so I do not worry about magazine issues.
Tools-You will need a barrel wrench for sure, after that there are different ways to work it. I have a barrel vice, and action wrench to go along with my barrel wrench, but I can use those other tools for swapping out Remington barrels too. I think if you are careful, you could use a padded (wood V-blocks) vice to hold the action. If you have trouble keeping the action turning in the vice, I screw in the action screw to help keep it from turning, once you get the barrel nut loose, you can back out the old barrel and switch the barrel nut over to the new barrel and tighten the new barrel into the receiver. I have used full length sized cases to set the head space, but a regular go head space gage works best IMHO. The case wants to squeeze down a little so you have to be careful not to tighten the barrel too much. It takes a little feel to tell when the shoulder bottoms in the chamber. The steel head space gage will not crush down so it is easier to tell when you have the correct head space. Just turn it down until you feel it bottom out then back it off a 1/32 turn or less. A 1/32" turn is about .002" head space. After you have it set, then run the gage back in to make sure it goes in and out freely. I then use a full length sized case to make sure it goes in and out easily. I get little case stretching and the cases go in and out real smooth. Getting the first barrel out is the hardest. After that, I put some anti-seize on the threads and do not torque it real hard when I set the head space, I just snug it good. After that, it is real easy to take it down and switch barrels. Good Luck and Good Shooting