I came close to buying a GLI before my first sportwagen. They were and are nice. As a die hard stick shift person i am in love with the DSG. It’s like hiring out your clutch and shifter work to the best driver in the world every start and shift. A VW well cared for can be reliable. I also owned a Regal Tourx with aisin slushbox and found that to be decent. So you cant go wrong, some VW models come Aisin and some DSG. The downside is a VW needs specific care, but if your on this forum you should be able to do that!
Thanks for the input. I was a die hard stick shift person till I got my first motorcycle around 5 years ago, now I have something that I can enjoy / play around and I don't have to suffer with my daily driver. Also, my wife can't drive stick shift so I should not really buy a manual car unless it's a dedicated track toy, which I have no budget/parking space for that, at this point of my life.
After deciding which type of car we're going to get in my original post, one of the reasons why I chose Jetta GLI over slightly used A4 is GLI is more capable of occasional track days/open lappings and features you get for the price under $40k CAD. It's more well-rounded not only as a daily driver, but also for more occasional spirited driving. It's not great at anything, but good enough in every category (performance, practicality, daily drivability) for my needs.
This is the first direct injection (non PFI), non torque converted automatic and even non Japanese car purchase of my life (first brand new car purchase with my own money), so I kinda hesitated at first. But as I do my own maintenance and am on top of my cars maintenance all the time, I think I can handle it going forward. Time will tell.
By the way, the GLI is at "Port Stock" status, meaning that it's in Halifax, NS. It should be ready in the next few weeks.