I have a 2008 A4 3.2, Ocean Blue Pearl Titanium, S-Line, Sport, 6MT that I bought new. It has 55K miles on it now. $45k new in 2008.
I also just picked up a 2010 S5 4.2 with under 15K miles, Prem+, 6MT, Rear Sport Diff. $40k 2 months ago.
My A4 has the RS4 rear sway bar and 19" wheels with Michelin Pilot Super Sport tires.
My S5 has Ecode Tuning front and rear sway bars, Alu Kreuz, 19" wheels with Michelin Pilot Super Sport tires.
I mod for handling first, then go from there, so with that in mind, here's my opinion...
A used A5 would be very similar to my A4 and a used S5 would be very similar to my S5.
There really is no comparison between the A5 and the S5, so I'd recommend the S5 if you can find one in your price range.
I'd recommend a 2010 or newer so you can get the rear sport differential (prem+) or Audi Drive Select (prestige).
Both '5s are real lookers but I think the B8 S5 is a notch above the B8 A5 in looks, YMMV.
If you enjoy driving the manual transmission, you have to get the 6MT. If you enjoy driving the automatic transmission, avoid the tiptronic and get an S-tronic/DSG (dual clutch automatic transmissions that are very smooth and very quick).
The pros for the A - A spirited drive, slightly higher MPG, a bit lighter steering wheel feel, and a bit lighter car weight feel.
The cons for the A - A bit under-powered, not as solid of a car (compared to the S5) feel but very polished.
The pros for the S - A very spirited drive, more power, more torque.
The cons for the S - slightly lower MPG, a bit heavier feel to the car.
You have to set your own priorities, or get both an A5 and an S5.
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