Well, I've had both, and can tell you that I'd rather diy the 911 than the 944, but neither unless I had a nice garage with a lift or at least something other than a floor jack.
The '44 is a mess of vac lines and other stuff that's in the way, plus they're not going to appreciate. If you need to pay a wrench, the cost is the same, so which would you rather drive.
The 944 is a better dd, but you have one of those...
Why not a Carrera? I constantly think about selling mine, but know that if I do I wouldn't replace it, so I'm holding on. For now. I could be persuaded