If you have been good at keeping up the maintenance on the Boxster and you like it as a daily driver, it is probably worth more to you than what you would easily get for it.
If you get a sporty 2-door car, it will probably get old having to put the baby (all too soon toddler) in the back. I'd highly recommend a 4-door. Also, babies need stuff, lots of stuff, and more of it every week. Make sure you have room to load it all up and that it won't be a pain to load/unload for the wife. My son had a 2 door Accord when my granddaughter was born and later moved to a 4-door V6 Passat. He didn't miss the Accord at all.
There are lots of good, safe and reliable baby-toting machines out there for $8-10K that should be great for the utility and extra space you will need. Get one that makes your
wife happy. ...and keep driving your Box.
Cheers on the new addition