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Maybe this will help give some perspective. Sorry, it's a little long winded.
I've been doing the "winter beater" for about 7 years and I just purchased my 2nd beater about a year ago for $1200.00 and I expect it to last at least three years, maybe more. I do expect to replace the AC compressor, and redo the valve cover gaskets, but I can do those myself, with a little help from friends.
They basically turned into my daily driver as I only have a 15 mile drive each way to work. This in turn, has fed my OCD about keeping my car clean and out of the elements as much as possible.
I think my age is trumping that this time around, as I'm now on my 4th new vehicle (FR-S) since this all began; while it's probably my favorite, I'm finding I just don't give a shit as much. The honeymoon is basically over after a year with this car. But, I still can't live without it being in the garage when there's crappy weather if I can avoid it.
I got to drive the FR-S all winter last year, at least once a week or so. That is, when all the snow melted, no salt puddles or salt dust were present. I think the longest it sat was about 10 days.
The first one was a 95 Corolla which I got rid of after 6 years (paid 1700). Picked it up with 80,000 miles and All I had to do was some exhaust work, brakes all around over a few years and a new set of tires. Not bad. It actually got rear ended and I got a check for $2600.00, kept the car, paid 400 to a body shop to pull the trunk out and mount the bumper again. Good as new! LOL. I sold it last year for $800.00
My latest, a 2002 Sonata V6 GLS, had 180,000 on the odo, but the entire front subframe and supporting suspension was just replaced under a recall right before I got it from a coworker for 1200. Almost drives like new, runs great, looks respectable.
That said, depending on your situation, if you want to go that route, it's not horrible if you know how to choose a car. Certainly there can be some surprises, and you'll have to plate and insure a 2nd car, but it's really all relative.
I like my toys clean and free of corrosion, and if I decide to keep it, all the better.
Some might consider that a little OCD. I used to lose sleep if I knew my toy was out in the elements...LOL I think I still might. My garage is being gutted and redone from some storm damage so my car will be outside for a week :/
The con here is an expenditure, and as you mentioned, you'll likely have some repair bills in that price range. But I guess, like I said, it's all relative.
What's more important to you is what you have to ask yourself. And, are you willing to shell out anywhere from 2500-5000 initially with insurance, plating, and routine maintenance to follow. Including the feared 'unknown' repairs.
You could spend that money on more mods for the toy and do the things you mention like undercoating, rust prevention, snow tires, etc.
The pros are that the car is going to stay cleaner longer and less exposure to road salt which means working on the car will mostly remain a pleasure for you, and your mechanic as long as you own it.
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