Without a doubt keep that 944! Unless you want to sell it... To me
In all seriousness the 944 is appreciating and it's becoming increasingly harder to find one in that nice of condition. You will make up $ you sank in the boxster in upgrades from the 944 appreciating. Wait about 5 years, save up to get an S. I would love to have a 944 like that in my garage to use as a weekend cruiser.