I am interested in following this topic as well.
I have a CZ550 varminter rifle in 308, so not the same thing as what you are looking for exactly, but other than the chambering, it is the same rifle as the 22-250.
The CZ rifle is really top notch quality. It is easy to mount a scope as there are dovetails in the receiver ready to accept any number of different manufacturer's rings. If you determine that you want an angled, picatinny, scope base, I think the Winchester would be a better start, as the resulting height above the bore on the accessory bases I have seen for the CZ would make the rifle a little bit awkward to shoot, I would think.
The CZ barrel is cold hammer forged, which shoots very accurately. I don't know whether the Winchester is CHF or button rifled. Some will say that the hardening of the steel imparted by the CHF process will render a harder, or more durable, bore, which if true, would suggest that with a hotrod cartridge like the 22-250 might allow you to eke a few more accurate rounds out of the barrel of such a rifle.
The CZ set trigger is a nice alternative, but truthfully I only use the standard, non set, trigger 90% of the time, and if the set trigger were removed, I don't think I would miss it any.
At first I was not enamored with the CZ detachable magazine, but once I learned that there are super high quality 10 round factory magazines available which fit perfectly, my opinion changed. Unless there are legal restrictions on number of cartridges that may be lawfully carried in your hunting rifle, the 10 round magazine is really nice.
The Winchester has an internal magazine if I am not mistaken. Some of the Winchesters don't have CRF, which is either a feature or a mistake, depending on your point of view. Too, the Winchester barrel is a little shorter than the CZ, again maybe you get an additional 60 fps out of the longer CZ barrel, all things being equal.
I would not hesitate to purchase another CZ550, if that helps you at all. It is my favorite factory bolt actioned rifle, and I owned a CZ527 (stolen) and a 455, so my favorable opinion about the CZ quality has carried over throughout their line of rifles.
My interest in the Winchester is to get a heavy barrel in 243 caliber, something CZ doesn't offer.