I would find a nice pre Model 70 Winchester rifle in .257 Roberts. If that was not do able, I'd find the same pre Model 70 Winchester... in 7mm Mauser or else (can i be this boring) .270 Winchester. I grew up reading Jack O'Conner's articles in Outdoor Life. I very much enjoyed what he wrote as well as his opinions.
The best early-production (first 20 years or so) Winchester 1892 or 1894 I could find for the money. Caliber wouldn't necessarily matter much, but I'd lean toward .25-20 or .32-20 for the 1892 and .25-35 for the 1894.
You mean like this one. It was made in 1893 but someone put a new 25-20 barrel on it. It is fun to shoot.
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Pretty sure the CEO has a sweet 9 mm Shield in his desk drawer. At least one drawer. I would try and get a evil black rifle for my grand.
Dan Wesson ECO or CZ75 Compact Sig P250 Two Sum