Be veeeery careful. The total number of Judges that you can find out there for sale far exceeds the total number that Pontiac built. Translation: there are a lot of fake ones. If you're looking for an investment, then a rare-optioned, original, numbers-matching car is going to be the best move as long as you can buy it at the right price.
If you're looking for personal enjoyment primarily and don't care so much about resale value, then don't worry about any of that - buy a car that appeals to you, is in the condition that fits your skill level, resources, and interest as far as doing your own work, then do whatever you like to make it "yours".
My 69 GTO is solidly in the second category. It's numbers matching and "original" (translation: I still have all the original parts that came on the car from the factory even though they aren't all ON the car right now.) However, it wasn't "anything special" other than being a real GTO. It had the "normal" GTO engine which was a YS-code 400 rated at 350 HP, automatic transmission, 3.23:1 non-limited-slip rear axle, A/C, power disc brakes, power steering, vinyl top, and AM radio. In terms of total production numbers there were probably more 69 GTO's made like mine than any other combination. However, when I "restored" it I nuked the vinyl top, put in a Moser 9" rear with 3.50 gears and Wavetrac posi unit, aftermarket suspension, exhaust, 4-wheel disc brakes, and "warmed up" the engine considerably. Result: "MY" GTO does very well at shows, gets tons of admiring looks and comments from "the public", and has run a best quarter-mile to date of 11.86 @ 113 mph. It's also very doubtful that it would bring as much in its present state at auction as it would if it were still 100% original. Not too long ago I saw a 69 GTO pretty much like mine was originally, still all original and in very good condition, cross the auction block and sell for just over $18,000. I've spent more than double that amount just building my car. But I don't care about any of that. I built it to please me, not someone else, and I don't ever plan on selling it.
So, it's your call.