A possible project for you If you look at the thread How we use our remaining classics, you will see a really nice looking 68 Lark that SportWagonGS has been using as a daily driver. He recently had it on e-Bay with a $3500 reserve and is asking $4400 or best. Looks like a good one to start with!
Why not consider the 'Larks big brother? Having owned about 20 Rivieras, Centurions, and Wildcats, I must say, you get a lot more for the money. If the wow factor is important, then look for a good old boattail. I got more looks in my triple black 72 than I ever did in my GN or my Skylark. Besides, with a Riv, you get a BBB (standard) (can even get a stg 1), and all the plush trimmings. And even though they look HUGE they don't weigh that much more than a skylark. If you are interested, LMK. I have a few in my possesion (one that's ready to drive--includes A/C) that are WELL under your budget! Jason Way too many Buicks to list.
There's Bud's 72 Skylark for $2000 (in WA). I've seen this car. It's a great drive-it-today, modify it tomorrow car: http://www.v8buick.com/showthread.php?s=&threadid=22758 The interior is immaculate in this thing! It's dark green, but it's in incredible shape.
Here's one in Dayton, OH for $2300 Or Best Offer: http://adcache.collectorcartraderonline.com/10/9/4/66264994.htm 1969 BUICK SKYLARK, custom, 69k miles, $2, 300 or best offer 937-890-2693 Dayton
Well, you could drive mine home to Indy and then shipping wouldn't be a problem. I know it's a 4-door, but it is a straight driver with working AC: http://www.v8buick.com/showthread.php?s=&threadid=33971 Drop in a 455 and you've got quite a sleeper. At this point I'd take $2k for it. - Freed