I'm not a huge fan of Cadillacs. Growing up, one of the most common and stereotypical Caddies was a 1977-1992 Fleetwood Brougham. It was traditional American luxury in the chintziest way. The body was big and old-fashioned, sitting on a full frame with super-floaty suspension and wire hubcaps and a padded landau top, all driving home the belief that this was a luxury car. Inside you got your typical complement of leather and fake wood in a color that tried to match or compliment the exterior paint. Top it off with whitewalls and color-contrasting pinstriping and you have the perfect car for the senior citizen of the '80s. By the time I was growing up, many were reduced to faded, broken second-hand daily transportation or pimped out cars for ballers on a budget. Cash For Clunkers killed off a slew of these cars, making them less common now.
The 1977 Cadillacs looked modern in their time, but in my opinion the design dated quickly and the cars looked ancient by the time their body shell was finally replaced 15 years later. It seemed like the company that claimed to be the "Standard of the World" for luxury couldn't engineer the right engine for the times, either. Early cars had monster 425 cubic inch V8s choked by emissions gear, then the awful computer-controlled 8-6-4 V8 (an under-developed forerunner of the modern cylinder deactivation system) ruined Cadillac's reputation for reliability. Then came a diesel 350 from Oldsmobile and a fuel-injected aluminum 4.1 liter V8 that was quite advanced on paper but in execution was prone to gasket failure and other maladies. Later cars on this platform used Buick V6s, Olds 307s, Chevy 305s and 350s. None of these engines produced more than 200 horsepower.
If this was my car I'd invest in new fender extensions and that corner trim piece, polish it all up and call it a day. Then go cruise.