First off I encourage starting a youngster on a single shot rifle that is the correct way to go. IF he is recoil shy you can get a small 22 centerfire barrel for it and let him acclimate to it slowly. The Encore is handier and a bit lighter than the Tikka. You will be surprised how fast you can get a followup shot off in a single if needed at all. Both are extremely reliable and accurate rifles . Later on he can get a caliber that will both kill deer cleanly and not kill the shoulder. You don't want them shooting a bruiser therefore the 7-08 and the 260 would get the nod here...there are comparable cartridges out there(250 sav,7x57mm, 6x55 etc etc) similiar rounds out there but they may or may not be available in the Encore. If you opt for the Tikka make sure it is within his physical abilities to hold it steady if not get something lighter. Browning A bolt Micro,Remington Model 7,Winchester lightweight and Ruger makes a lightweight would be good alternate choices.