new hear, but here goes: Up here in the Great White North ("it's a beauty way to go"), lots of cars are bought as "daily drivers", unrealistically. I live in a pretty reasonable part of the country (only -40℃, or -40℉ a few weeks of the year, and a desert as well), and some people think that they can use a classic car for everything. This is simply not the reality.
Some cars that do come to mind that could suit you well:
mid/late 1960's Mustang. There may be a few that have been updated with better suspension/brakes, etc. One of the "coolest" cars I recall seeing around here was a early "Comet" Rancher, with a 5.0 transplant and updated suspension and brakes. It is one of the few standouts that could actually be driven (almost) year round. The same could be said orf an updated Comet as well, if a 60's Mustang is out of the question. I've seen some very nice "Shelby-ized" cars that could also suit. Cost of maintenance and repairs is very low as long as you don't end up with a thrashed car that needs a lot of repairs to start with. Update as $$s are available, and understand that you may never see a return on investment, it would function as both a "toy" and a daily driver.
Consider the SC300 Lexus coupes. Big, luxurious and "sporty". Well within your budget. I even know where one is available (Las Vegas car its complete life, obviously rust-free, always maintained , and still in 'Vegas). I recall that the big 3 review mags of the day suggested it was always a better car over-all than the SC400-lighter, and thus better handling, better on fuel and just a touch slower than the V-8)
And to all that have suggested a Volvo Amazon, 140 series car, etc: I agree completely here. Built like tractors, can be made to handle and brake well (did GRM do a 122 2 door as a project years ago?), performance is available and essentially invisible if not "flashy. Another alternative, which might me my pick) is a P1800 either coupe or wagon, for the same reasons above.
Just a couple of thoughts.