Congrats Aaron!
Nice looking car with an awesome history. It was nice for you to keep it in the family. Does not look like she needs much work at all!
If the carb has never been rebuilt, then the black smoke and hesitation could stem from there. 22 years on the rubber parts in the carb is a LONG time and they do rot from age and constant contact with gasoline...
Nice thing is that you have no computer controls and you do have the service manual. A carb kit is maybe 60 bucks and if you can take a clock apart and put it back together (and it works afterward) then you should do fine rebuilding the carb.
Again, welcome! You just caught the Olds disease!

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-Rob Young
1972 Cutlass Supreme Convertible (442 clone) -"Lady" (My mistress...)
http://www.flickr.com/photos/robsalbum/sets/
1986 Cutlass Supreme Coupe - "Pristine"
1978 Ford (Old Faithful) a.k.a. "the Tramp"
1997 Cadillac STS (for sale - too many cars!)
1999 Harley Davidson Sportster - "the Freedom Machine"