You see, that's fine and all Bill, but the part you're neglecting to put into perspective here, is that you've already got a better than average Cobra parked in your driveway. That's more flash, or sports car than 90% of the members (myself included) on this site have.
When I was referring to a more practical daily, I was thinking something along the lines of something newer, with warranty, interior space and little gas mileage in mind and replacing your now 12-year-old (and seemingly problematic) Mark VIII with it.
Sure, a GTO is about as "Flash" as a Cougar, but the missing part of that statement is, that if I had the chance for a Cobra or even a GTO right now at a price that fit into my budget, I'd dump my Cougar in a heartbeat....but I'd still have something semi economical as my daily.
I wouldn't keep the Cougar, buy the Cobra/GTO and pick up a daily?
It’s nice that you've got some money to play with, but let’s be honest...in this economy...$50,000 really still isn't that much money. And with your luck, I'd be keeping as much of it around for a rainy day that I was able to. You're not working right now, am I correct? Or if you are working, it's not paying the kind of money you would consider "comfortable" or what you would like it too, right? Cars in general are a bad investment and if you don't need to be buying them up like candy (especially cars with similar classifications) when you cash flow isn't regular, you shouldn't.
With the up and down that your father often is, it probably wouldn't hurt for you to be preparing for a rainy day there in the event his heath gets worse, or if the next car accident he has isn't his (or someone else’s) last.
Again, this isn't a quit pissing away your money response, but not more than a couple of months ago you were hurting. It can go as quickly as it comes. I for one would choose necessity over luxury at this point.