The thoughts of spending $2K on a Winchester makes me nauseous.
You didn’t even mention the intended use or desired caliber.
Regardless of the answers to the previous questions- Winchester is not the answer
When they were still made in New Haven, Winchester was turning out some good looking rifles that were also very accurate. I have 3 of the classic model rifles and they are all sub MOA guns. My Stainless Classic 300 Winchester Magnum is a .5 MOA gun or better with Berger VLD bullets.
I hate the trigger on the post New Haven, FN produced M70 rifles. The barrels are also not the same quality and I think they use silly putty for a bedding material.
If i need another Winchester, I'll be looking for older guns and pass on current production rifles.