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As someone who has driven several versions of both cars in question, I will say it's quite possibly one of the hardest between-two-cars decision one could have to make.
Now to answer the question. The 911 is clearly the superior car. It is more engaging, has a superior chassis along with steering, brakes, and handling. It's more precise, more communicative, and definitely the better of the two to wring out down a twisty backroad. If you have kids, the back seat could even be a big point. It will definitely be more reliable, and it will definitely hold it's value better, at least for the immediate future- 3-5ish years.
That said, and something you pointed out, no 991 short of a GT car even begins to approach the charm and character of a V8 F Type. The engine is glorious, with Herculean power and a sound to wake the dead. I honestly think aside from lack of a back seat, it's no less practical, and no harder to daily drive. It's quite a comfortable car, and though visibility isn't as good as a 911, it's a very easily managed car in traffic and whatnot. Though the interior definitely leaves some to be desired, I think the dead sexy body it's wrapped up in makes up for it. Also, though it may have inferior driving dynamics, I think it's actually more fun on the street in and urban area because of the engine and power delivery. I personally adore the F Type, and like you said, I've never emerged from driving a V8 one without a huge grin plastered on my face.
At the end of the day, unless the rear seats were a major factor, I don't think I could buy a 911 S over an F Type. Not a PDK car, anyway. If it were a perfectly spec'd manual, there might be more contest. My pick of F Types would honestly be an earlier RWD convertible though.
Ultimately, you can't go wrong either way. Just enjoy whatever you end up buying every chance you get!
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