Hello Jody! Hope you're doing well.
To the OP - I'm an AP1 owner and a C2S owner and have had some seat time in Cayman S/Boxster S and non S models.
I was originally going to sell the S2K after buying the C2S but unless I swap it for a Lotus - I'm keeping the S2000. It's waaaaay too much fun.
All great cars - but it kind of depends on what you want. The S2000 has more of a go kart feel and the 9,000RPM redline of the AP1 is fantastic.
The Box would be a better daily - it's more comfy and torquey. On track/auto-x they are very close - it's really down to the driver vs. driver rather than the cars themselves.
IMO the Boxster is a bit more forgiving at the limit.
You just have to drive both and see what you like better. The Honda is a Honda. It is going to be very inexpensive to run/fix/maintain etc.
The Porsche - I can't even see the engine.
Better to have a newer CPO car if you're going the P-car route.
Sloopy - you are incorrect about the S2000 weight distribution - the Honda is a F/M car with 50/50 or 49/51 (depending on the source) weight distribution. The engine is not between the wheels - it is set back towards the firewall.