Any old Caddie is a wise choice for driving for the pure pleasure of driving a classic. However, there will be constant challenges driving and parking. I say go for it.
Wise choice for owning*
Not necessarily daily driving...
My 1st car was an 82’ Eldorado, and even 24yrs. ago it wasn’t exactly a smart decision of mine to pick that as my 1st car and daily driving it.
But for someone to attempt that today, with a nearly 40yr. old HT4100 under the hood, it’s seriously only a matter of time before it completely implodes. Most would consider it a small miracle that it’s lasted 38yrs.
Don’t get me wrong, I still have a soft spot in my heart for those cars, but the only way I’d buy 1 today would be if I had a garage to put it in, because that’s exactly where it’d spend about 90% of its time. And I’d have new engine money set aside just waiting for the inevitable day.
But there’s no way in hell it’d be my only car/daily driver in the present day.
P.S. There’d be absolutely no challenges “driving and parking” the car...