I would buy almost exactly what I have now, a new 718 Boxster. If I did not need to have some semblance of responsibility in my head with respect to how I spend money, I would buy the S. Last year when I ordered my Boxster, I did not perceive a jump from 300 to 350 HP was worth almost $10K and I do not regret that decision at all. However, I would not complain about an extra 50 HP if I could at least rationalize (that does not mean justify) the cost of it. In all cases my Boxster is exactly what I want for a daily driver and coupled with a mid sized X3 SUV that sits mostly unused in my driveway I have the best of both worlds and don't see how money can change that.
I based my decision to not get an S on 20 years experience with Z3/Z4s. These were slightly heavier cars and had engines, depending on the model, advertised from 225 to 265 HP. For daily street driving with a manual transmission, I was able to get the thrill I needed. The Boxster with an advertised 300 HP and a bit less weight than the Z3/Z4s I thought would do even better (and it has). So, almost $10K just was way too much buck for the bang. I certainly would have gone with the S if it was less but it is impossible to say now at what cost I could have rationalized it (maybe $4-5K?).
Whatever I would get would have to be a convertible. I almost certainly would not look at one of the 911 variants. I perceive the Boxster is somewhat less refined than the 911s and for my daily driver that little rawer feel, with a large dose of luxury and electronics, is the right balance for me.