I have a 944 and a 924S along with my 911SC. For me the 944 was my DD in college and briefly after. Although I would love to have driven the 911 every day the 944 was more practical. Even by today's standards its not terrible on gas, it has modern accoutrements like AC (which my 78 SC does not) and is generally a very user friendly car. That being said the 911 still saw plenty of use even some daily use in there I guess it just depended on mood. The 911 is obviously faster and more fun but the 944 has its moments as well. I have recently been thinking about moving to a 3.2 911 as my DD.
The 944 crowd is also a bit different than the 911 crowd.
I guess the best way to put is when I was feeling like this I drove the 944
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but when I was feeling like this I drove the 911
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Regards
Dave