Good job on helping your friends, they now know what they can do with their rifles. My advice for your buddy with the 06 is if he doesn't reload to buy some different brands of ammo and see what his rifle likes. It's a lot cheaper than a new rifle, not as much fun, but cheaper.
I have a M70 that I bought new in 1977 that shoots Federal 150gr soft points great and they are a hammer on deer. My longest kill was 275 yards, bang, flop.
A few years ago I had surgery on my shooting shoulder and couldn't take the recoil from the 06 so I bought a new Savage M16 in 260 Remington. It was horrible, 2-2 1/2" at 100 yards. Sent it back and Savage rebarreled it, 1 1/2-3/4" at 100 yards. I rebarreled it with a Shaw 1-8 twist, 24" standard contour and now it shoots 1/2' or better at 100 yards with my reloads.
Here in my part of KY we can kill one buck and unlimited does, you do need extra tags though. IIRC you can kill two does along with a buck on your initial tag, will have to check that one out.