I don't have one now, but I have had at least one of all of the 250/255, 270/275, and 190/290 series Winchester .22s. The only one that I haven't had is the 150.
I think that they are good, but not great, rifles. They are rugged and reliable, the worst thing about them being the triggers that seem to be either mushy or stiff.
I have the 275 pump gun in .22 MAG and despite the trigger it is one of my favorite .22 MAGs. I don't care for the pistol grip geometry on the 150/250/255, too straight for me, but when I don't have to work a lever, the 270/275 and190/290 seem ok. I have the same stock geometry issues with the 88, doesn't work well for me, and the 100, works fine for me.
When Winchester dropped the blued steel 61s and 77s in favor of the 270/275 and 190/290 people were up in arms and avoided them like they would have avoided a syphilitic whore. There is no question in my mind that the 61 and 77 were nicer rifles, but they were more expensive to build and Winchester needed a line of .22 rifles that were more competitive with Remington's 500 series and the revolutionary for the time Nylon 66.
Not too long ago, GPC had new, old stock, deluxe wood for these rifles, some of it with amazing figure. I bought four or five sets of it for my 270/275 and a couple of 290s. I should have bought another couple of sets just 'cause. The deluxe stocks are GPC # 1528620 for $61.50 and the deluxe forearms are GPC # 1219110, but they are showing out of stock.