You will need to be more specific as to the model of Winchester rifle and which caliber it is chambered for.You will also need to include the overall condition of your rifle so that a value can be determined.
Best will be determined by intended use, your pocket book, your skills and what is available
a .22 caliber
A .177 caliber air rifle has very little recoil.
.223 caliber or 5.56mm.
No You could build a rifle in .306" or any other caliber but you are likely referring to 30.06. A 30.06 rifle is referred to as "30 Caliber" but to be accurate it is nominally .308"
Yes, I can. A Barrett M107 is a .50 caliber sniper rifle.
The Dragunov (note corrected spelling) sniper rifle is in caliber 7.62x54mmR. This is the same caliber at the Moisin-Nagant 91/30 rifle.
50 caliber
Can't be determined from the markings you list.
value of a model 49 ithaca 22 caliber rifle
You will need the services of a good gunsmith.