I know the feeling. I also own a 2017 S3 and every time a new improvement is comes out, or a feature added, I have pang of regret and question whether I should upgrade. Features and 7-speed aside, I think the Golf R is way too anonymous. There something "special" about driving the S3 that you just can't get with a VW -- a combination of the prestige of the Audi brand and the exclusiveness of the S badge. That said, it's the transmission that's caused me the most grief. For my previous car (a 2011 A4 S-Line), I lucked out and got into the first model year with the new 8-speed tranny, whereas 2010 and before only got a 6-speed. But in the case of my S3, I felt super short-changed when they announced the 7-speed for 2018, only a couple months after I bought my car! So my debate was: Is it really worth upgrading? Short answer: No. I don't do too much long-distance highway driving as it is, so fuel economy difference is almost a non-issue, especially the way I drive! The car doesn't really even drone at highway speeds even with resonator deleted. So, buyer's remorse fades and you find a happy place. You can only make decisions on available information and there will always be something better around the corner. I plan on driving this thing like I stole it for as long as I have it and enjoy every moment. Consider doing the same.
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