I currently own a '69 GTO, Red on parchment, loaded, and i mean loaded.  I also have a 2009 G8 GT, Liquid Red, modified to 470 rwhp.

I'm considering adding one of the following and am open to suggestions.

1989 20th Anniversary Trans Am same basic engine as Buick GNX

2006 GTO, manual, red

2014 Chevy SS 

Now that I live in the boondocks, a manual trans is desirable.  I know, other than the TA these aren't technically Pontiacs, but I'm old and like my modern conveniences.  Fireproof underwear.  Go.

 

If getting the manual is preferred, the TA or GTO are the options. The SS simply doesn’t come in manual  .  If you’re looking to drive and have fun with minimal maintenance, the newer cars may be better (of course depends on their conditions and past). 
 

If you like Pontiacs and classic cars though, can’t beat the TA. 
 

Ultimately comes down to what you’re looking for. All fantastic choices IMO. 

The TA is a 4 speed no auto.  Apparently, GM, couldn't field a manual stout enough for the TA, GTA, or IROC Z28.

 

16 hours ago, Kartattack said:

The TA is a 4 speed no auto.  Apparently, GM, couldn't field a manual stout enough for the TA, GTA, or IROC Z28.

 

That’s correct, the GNXs were paired up with a strong 200 4R overdrive transmission. No manual was available with the turbo 3.8L from Buick or Pontiac. GM was afraid people would blow the motors back when paired with a manual and it would get charged to warranty. 

I say get the GTO for the fun and more modern conveniences. Get the TA for the HP, fun, and long term value. 

Cant top the 69 GTO i would go for the 2014 SS. what color?

I have done limited touring with the GTO, but was always concerned about theft.  The newest toy would be used extensively for touring.  Not sure any of my choices are safer.

 

Th Chevy SS is probably less known to the general public as a performance car. 

16 hours ago, Kartattack said:

I have done limited touring with the GTO, but was always concerned about theft.  The newest toy would be used extensively for touring.  Not sure any of my choices are safer.

 

There are some very good ways to prevent theft of the newer cars, and the best is if they can’t start it they can’t steal it! Unless they have a tow truck! There are some good companies out there that sell remote controlled relays for the ignition. Or the easiest is just break one leg of the brake pedal safety switch. Take that leg to a hidden 12v relay and the to a hidden momentary switch! But pick the car you like and want!