I came from a B8.5 S4 that was dual-pulleyed and also a manual (no coupes for me).
Car was fun, I do miss the instant reaction of the supercharged 6 and also the manual input of shifting clutch when not stuck in traffic. The B8.5 had literally every mod you could put on the thing save for a ported blower. The B8.5 S4 and the B8.5 RS5 are very similar save for the engine and the typical RS treatment (wider fenders, bigger brakes, etc). One of my closest buddies works for JHM and we'd go back and forth driving my car then the shop RS5 - Very different attitudes, similar power levels, similar E/T (both ran mid-high 11s).
I've since moved on to a 2022 RS5 SB. Car has the RS Sport package, RS Driver Assistance, and a ton of mods. As mentioned, there's not as much soul with the B9.5 - That being stated, it's literally better at everything (comfort, usability, handling dynamics, looks, reliability, tech is awesome, and the sound system is significantly better).
In my opinion, B8.5 to B9.5 are VERY different cars driven by two major categories -#1 Engine (similar power levels, but that 4.2 screams) and #2 Next Gen Tech (technically 2 generations newer on B9.5).
For me, if the intent of the car is to daily drive, B9.5 RS5 100% of the time. If the intent of the car is track toy, I'd lean towards the B8.5... Who are we kidding, the B9.5 RS5 is pretty close to a $100k car all in, lots of cool stuff you can pick up as a track toy at that price point or less which would all but shit all over the B8.5 and the B9.5
Last thing to think about - The cars lost some soul moving from B8 > B9. We're probably in for another soul-neutering when we go from B9 > B10 with new power plants via 4 Cyl and likely a mild PHEV.
Good luck.
-DL
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