I have read posts on other sites that say yes, but you have to be concerned with velocity and bullet performance. How fast you are shooting what bullet to get the desired expansion/penetration, but I am sure that you would research all that anyway.
Absolutely. If I remember correctly I had one of the early Contender loading books with the 357 herret and other contender chamberings. If my memory is worth a hoot I think there were spitzers being loaded in the maximum back then. I think I tossed that manual when I moved last time because it was in bad shape. I will look for it next time I am loading.
Not a problem on the .358. Depending on design and twist rate you could have stability issues.
At one time I shot .311-.312 jacketed bullets through a blackhawk 30 carbine because I liked the bullet design. They shot wonderfully. No doubt there was probably some increase in pressure but I never saw it on the primers and I ran the exact same loading as for the .308 bullets.
As always this was safe for me and you are on your own to decide.