IMO, you gain a little more power with a 375 ruger over the legendary H&H, but not enough to warrant selling one for the other. The two ruger cases are capable of fitting in 30-06 actions, where as the full length H&H needs an action to handle a 3.600" OAL round. Winchester long actions already do this, and finding full length actions isnt too hard or pricey, so the need isnt there like it would be say 30 years ago, IMO. For the last few years, the 416 Rem mag languished, and was disappearing, so the new ruger had a legit purpose. Now Winchester is selling the safari rifles again, and ammo is coming avail again. Finding brass or ammo is fairly simple for the 375H&H, just about anywhere in the world. The new ruger cases, good luck. With the H&H case, you can make just about any belted mag from it, ie 7mm STW, 358 STA, 8mm mag, 416 mag, just to name a few. If you have a H&H, and want a definate improvement, have it reamed for 375 wby, and it will still take the old case with ease, fireforming new brass in the process. If you want the ruger flavor, then go for it, their alaskan rifle is cool. Only problem is, I dont think in the long term(15-30 years) ammo will be around. Time will tell on that.

I'll also add, unlike other guns, you do want some meat, aka weight with these calibers. It will tame down the recoil. I would think 8.5-9lb to be a good weight for a 375 or maybe a 416, and not be unwielding. Hence I rather have a full sized action, and not an intermediate action.