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23k sounds like a lot for a 12 year old car, even a pristine M3. But money aside, I just passed my '02 330i to my daughter in October and got a '14 335i for myself, so I'll give you my thoughts comparing the two.
First, I loved that E46 and I'd still be driving it if my daughter hadn't claimed it. The main high-level difference is that the E46 feels very analog, while the F30 feels very digital. What I mean is that everything is very linear and smooth with the E46, where the F30 sometimes isn't.
Some examples. The steering in the E46 is very linear. No VSS variable rack. No lighter effort in parking lots. No button to adjust steering effort. It is what it is, and it's always what it is. Throttle and engine - aside from a twitchy tip-in (this was BMW's first effort at throttle-by-wire), the throttle and engine are pure linear, analog joy. No turbo lag, no early torque, no disconnect between rpm/sound/torque. As rpm's build, engine sound builds, and torque/speed builds. This is the gestalt that we're missing with the early and flat torque curve in the turbos.
One other high-point of the E46 is the awesome visibility. The hood is so low is disappears. The belt-line is lower. You just feel like the greenhouse is much larger. And the car overall is smaller and lighter too. One last thing that may just be me, but I find my 335i's low-speed behavior to be jarring. The E46 is very smooth and behaves like a normal car at low speeds, where the F30 (auto) can be a bit jerky and cranky.
Now some downsides. The E46 has more road and wind noise. The suspension is more harsh. The back seat is smaller (but usable). Various components will start failing. Water pump, fuel pump, gaskets, boots, hoses, belts, radiator, etc. You also won't have any smartphone integration, although you can get a bluetooth adapter to play your tunes.
Tough choice overall. Personally if I was going to spend that much money used, I'd get a cayman or 911. But I hear you on needing a backseat.
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