Thank you all for the responses!
Cost issue: The cost of moving into an S5 this year would probably end up being 27k over the next 3 years. If you offset that by tire change/clutch change and worst possible scenarios for 1er maintenance it would drop to about 20k spent over 3 years. That seems like a lot of wasted money. On the other hand, it's a definite upgrade from the 1er and the added practicality and comfort is worth the money.
Tires: I've thought about replacing the run flats with non-run flats when they're worn out, but the lack of a spare worries me a little. If I end up keeping the car, i'll probably try that anyway and get an inflation kit. Also, The StiG, I have blizzak lm-25 rfts right now for snow tires.
Golf R: The car would be a perfect choice because of the awd and the fact that I absolutely love the GTI, but it's missing some things that I've become accustomed to: like automatic headlights and wipers, dimming mirrors, etc. On the other hand, I've always kind of wanted a sporty hatchback and if the subaru didnt look so outdated I would've bought one. If I go with the S5, it'll be hard to find a hatchback to get after that.
I could also wait for the 4 xdrive coupe to come out sometime next year or the end of this year but I'd probably have the same problems I'm having now with ride comfort.
Lastly, a winter beater is actually not a bad option. Anyone have suggestions for a reliable (and cheap would be great too) winter beater?