Questions:
1. Did you ask your FIL to sell you a rifle, or did he offer to sell them to you?
If you asked him, he probably doesn't want to sell his rifles, but would if pressed, as long as he can replace it for not much more money.
If he asked you, he either needs the money, or wants to help you, or doesnt' really know the value of his rifles. I doubt that he's trying to take advantage of the relationship. In either case, you need to tred lightly. Whether you like him or not, he's inextricably connected to your wife and if she loves him, your choices are limited here.
2. Do you like your FIL or do you want to insult him by not accepting his offer? This could be a rift-producer, no matter what you decide. If you like the rifle you choose, the money doesn't matter, but it may eat at you. If you don't like the rifle and trade it, you might cause a rift.
3. Do you want to keep peace in the family, or is a $50 savings worth sleeping on the couch for a month, or worse? Your wife is part of this deal, whether either of you want to look at it that way. You don't want to tick her off, so buy a rifle and take your lumps. That rifle could be the best shooter you've ever had, or have a burned-out barrel.
My advice: The Winchester may gain in value over the years because they're not being made any more. Can't figure why it wasn't scoped. A bolt-action .22-250 is not a rifle that anyone in their right mind would own and not put a scope on.
The Remmie may shoot better than the Winchester, but you won't know that until you scope the Winnie. Shoot the Remmie and if it's a winner, buy it and offer to give him first refusal if you ever want to sell it.
Picher