I always go in this sequence while selling a vehicle: Private party, Carmax / Carvana and the last option would be dealer trade in. Any specific reason why you dont want to sell the vehicle privately. Difference between private party and dealer trade in when i sold my 2016 GTI (2 years old with 26k miles in a great condition) was around $4k.
Your GTI has gone through major depreciation and it would not be any terrible in the next year or so. People claim that Rs dont depreciate as bad a GTI and it might hold its value better with People's warranty. Swap might be ok in your case if the money which you are adding is not going to make a dent in your overall financial status.
So why are you considering a new GTI / R to begin with.
I did check with carmax around the same time as I started shopping dealers. They were on the lower side of offers.
The extra hassle is the main reason for not private party selling. Though I am considering it more... definitely if I feel like I can get a good deal more money out of it. I’m browsing auto trader etc. gauging values, and trying to calculate depreciation on a new GTI or R. I don’t mind doing it, just have to be in a position where I don’t feel like I’m going to be throwing a bunch of money away. I thought I’d have at least 4K by now equity in this car given the deal I got and down payment. It’s sort of a value balance. Everyone has their own I guess. I could go all YOLO on it, but trying to stay smart about it.
Main reason I was considering a new car... I liked the R’s. I like the extra warranty. I like the GTI updates as well enough to consider having a similar, or hopefully lower payment ( $460 now) for another year and half. I would probably do the R at 72 months to keep payment close-ish. If I feel like it’s depreciation is slower as well. The lease values are much better percentage wise after 3 years, so hopefully they should. Fun car is also part of intertainment budget lol!!!
Doing a bigger turbo and tune, or a big e40 tune and budgeting for repairs keeps creaping into my mind lol, but this is a daily and needs to stay pretty reliable and have some kind of value. That’s part of the R as well. JB4 or APR+ makes it faster and the R has lower suspension and better wheels already. Something the GTI needs.