I'm not sure how much the the coupe iteration changes the delta between the two models. But, I drove the M235 convertible and the 435 droptop when I was shopping for a new convertible. The 4 was certainly more commodious, especially when test driving with spouse and 11-year-old child. It felt more grown-up and luxurious. Nicer than the E91 328iT, I was coming from.
What stopped me from buying it, was it just wasn't a lot of fun to drive. The 2, on the other hand, was a hoot. Quite similar to the car I miss the most, my 2006 E46 M3C. The 2 had a similar lightness and tossability. Driving it put a big grin on my face. The 4 was just pleasant, like driving a large sedan that also had a top that goes down.
I couldn't see paying $10-$15k more than the 2, just to get a droptop upgrade of my wagon.
All that said, I do think the 4 convertible is great looking. Better looking than the 2, which is a bit on the chunky side.
At any rate, I haven't regretted my choice a bit. It may also factor in that the other car in the family is an F15 X5 50i, so we have the privilege of a luxurious family hauler when we want one.
And I agree about weighing in what kind of driving you do. If I were on the crazy Atlanta highways all the time, I'd opt for the 4. Or, frankly, a tank. (Which is where the X5 comes in, because my spouse has that kind of a commute.)
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