Those aren't long hauls.
And are you the only one on the trip and how much stuff is the other passenger going to want to be bringing along? Do you value top down driving? Are you going to get a hardtop which does provide more headroom and cut down noise a bit? Aren't the 996 and 986 almost identical in firewall-forward design and so why would the steering be that different (could it have been alignment)? What years are you considering for both cars?
I've taken several 400km trips in the Boxster and I find it comfortable. Lots of luggage room, not much room for stuff inside the cabin which I find OK but my wife likes her things cluttered around her. OTOH, my wife doesn't like it as she feels she is sitting on the road.
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