How often do you consider trading up to a newer Boxster?

[WhipE350]

I've been looking into it seriously. My issue is more I want to drive a Porsche more and with hip issues I simply can't drive either one of my manual Boxsters enough and it frustrates me. I have a buyer for my 2007 and he will be getting an amazing car that is like brand new. I worked with my Porsche dealer for a 981 at 7.5% off MSRP which makes us both happy but I haven't moved on it yet. If I get another Boxster it won't make sense to keep my 986 unless I plan to track it or send it up to my Mom's house for my summer vacations. I've also been looking at the Cayman 'S' and 911s. I want something I can drive to work a lot and take on long weekends without having to worry about shifting a manual. Well anyway not sure where I will end up, I know for sure if I have to part with my 986 someone will get a totally bullet proof car after all I have done to it.