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I would pull the trigger on a replacement for my 2009 model.

Got an 8 core now so would like 12 - 16 core, 32GB RAM (got 16 now), and all SSD. I have mostly SSD now. I'd love to run one of those Accelsior PCI SSD disks from OWC as my boot volume, and then RAID 4 internal SSDs for data storage. And then a thunderbolt external for time machine/backups.

I have no real NEED to upgrade my 2.93Ghz 2009 model - but one can't help but want the latest and greatest. I could palm my current workstation off to my junior. She would love that.
 
None.

I bought a 3.2 Ghz Quad-core model last year, and it is currently serving me well. I'm musing about upgrading it to the 3.33 Hex version, but am a little skittish, and more unwilling to commit to the downtime.

It serves me loyally and well, and if I had the cash to spend, I'd spend it on RAM upgrades and the like.

I will however say two things:

1. It would ensure the laptop purchase I'm about to make has an Apple logo on it, since I wouldn't be taking the first steps towards abandoning the platform.
2. A year from now, I'd be trying to buy at least one high end Mac Pro a year or so from now.
 
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