1988 Cadillac Fleetwood
Brougham

Automatic
5.0 / 305ci V8
Carb'd
RWD (because I guess some of the fleetwood models were fwd)
about 150k miles (odometer doesn't work)
I have the following issues and explanations:

It had been sitting for 7 or so years in the elements...so its extremely dirty, and a little rusty. It was taken to a local mechanic before I bought it and the owner had a list of things that had been done to it.
"Winterized" Though I can't really tell wtf was actually done other than a top off and lube job.
Brake inspection
Exhaust piping replaced due to rust
Alternator replaced
belts and hoses replaced (actually pretty thorough)

Since I've gotten it (paid 500$) I've noticed that it is leaking oil pretty bad. Having to add about half a quart per day. Driving it back n forth to work about 120 miles or so round trip + around town. It is also leaking antifreeze from what I believe to be the freeze plug on the driver side near the firewall. Pretty much all the seals seem to be oozing oil, which makes it difficult to track down the leak. There is no smoke from the tail pipe, but after the engine is hot there is a bit coming from the top of the manifold.

So here is my question to the forum... Cut my losses and scrap it, or fix it and drive it til the wheels fall off?

for the amount u would spend changing gaskets/rebuilding carb/hoses/plugs etc

you could buy a decent used 350.

Have any idea whether or not the auto tranny will mate properly? I've got no idea the specs on it...I'll have to look it up.

yes its a chevy motor.

A 500 dollar car is a disposable car, buy a roll of duct tape and try to seal off the leaks.

This. It's probably got a 350 tranny in it. It should bolt.right up

305's are generally garbage

.02 given.

They run forever but dont make shit for power. Some people choose to build them as high reving n/a motors but it takes alot of $$ for a little bit of performance.

They sound so badass pushing 8k revs though lol

You could break even if you scrap it and sell the cats.