A 223 can be a lot of fun shooting at Jack Rabbits and in the winter time the little desert cottontails.
On the other hand the 300 Win woulld be a nice long range mule deer and elk gun. Ruger #1 are notoriuosly finicky about fore end pressure and can be hard to get to shoot really tight groups. Ask him what his groups are like and what he does to tune the foreend. There is a device called a Hicks Accurizer which he may have installed. Because of foereend pressure the gun will have a tendency to walk as the barrel gets hot. Hunting, it is not a problem because you don't shoot enough to get the barrrel hot, but it is frustrating to try to shoot good groups at the range or when you get to shooting drops.
At some time in the 1980's the Ruger trigger was changed and is no longer adjustable and is pretty stiff. Prior to that they were (at least mine) a dream to pull once you adjusted them.
I suspect that if you have to ask that you are not really a #1 type of person. I think you just have too love the gun and really want it to be happy with a #1 and tolerate its quirks.