As to the idea of collapsing the iMac and iMac Pro lines into one using the iMac Pro case and cooling, it would be feasible and possible.
The W-Series Xeons are just the X-Series Core i9's with ECC RAM support so Apple could conceivably just smash the lines together - I expect ECC RAM is not really critical to most iMac Pro users, but it is what comes with Xeons. Intel did launch the 10th Generation (Cascade Lake) X-Series last fall at 10, 12, 14 and 18 cores and all are at 165W TDP and priced at less than half of what the W-Series were.
Apple is clearly seeing significant drops in NAND storage prices which is why they have been doubling their base SSD capacities. So I could see them dropping Fusion Drives in favor of 512GB SSD as the base level of storage. The iMac Pro case (including cooling) also likely costs more than the iMac, so I could see Apple raising the base price by at least $100 to cover all this. Maybe raise it $200 and bump base RAM from 8GB to 16GB. I mean people are going to erupt over the loss of upgradeable RAM so might as well raise the price, too. 😛
And when you consider adding 16GB of RAM and a 512GB SSD to an existing base model 27" iMac is $500, paying $200 for it is a deal. 😎
So where does this leave the iMac Pro? Perhaps as an option package instead of a separate model?
MCK says a 27" miniLED display is coming so what if it becomes a BTO upgrade option like the X-Series (12-18 core) CPUs? Same with 10GB Ethernet? And workstation-class GPUs?
So you have the "base" 27" iMac with the 10500 Core i5 CPU, 16GB of RAM and a 512GB SSD for $1999 compared to the current 8500 Core i5, 8GB of RAM and a 1TB Fusion Drive for $1799. I like to think that reasonable people would find that a reasonable deal.
From there you can add RAM up to 256GB, storage up to 4/8TB, faster Ethernet, workstation-class GPUs and miniLED display.
The iMac Pro isn't a great value at the low end up against the Comet Lake S CPUs. If Apple should choose to go with the iMac Pro cooling system but design a Comet Lake S system, compete with 125w thermal TD CPU SKUs to slide right into the iMac Pro case which was built to accommodate Xeon W21xx class 140w CPUs.
The iMac Pro uses RAID pairs of SSDs so low capacities are uneconomical even though the performance is very strong. There's a limit to how low cheap the Xeon setup can go despite cuts in the price of NAND, RAM and the Xeon CPUs.
If it was to stay in the Apple ecosystem it would have to be with the 12 Core version as base model - going beyond the capability of Comet Lake S to compete. The storage could be doubled by default and RAM could get a boost too.
Therefore there would be no price cut but enough spec bumps to make the $5k price tag relevant again.
The iMac Pro stays a sensible choice if the iMac redesign includes Comet Lake H for consolidation reasons.
A price increase to the standard iMac 27" would be inevitable with the the transition to all SSD, the T2 CPU would have to be added too so your price estimate might need to be extended up a bit. This would also open up space beneath it to include a 23" iMac.
The standard iMac 27" may need 1Tb of SSD storage though - it depends just how important the marketing department see the storage level in the 27" - and may also be a clue to why the 23" iMac may be needed.
Or they switch to Mobile CPUs and leave the iMac Pro as a separate high end model.
I already suggested a situation where Apple use Comet Lake H in a world where shrinking desktop unit sales give Apple the excuse they need to use the same processor in the iMac (following a full redesign), Mac mini, and MacBook Pro 16".
To add to this, Tiger Lake H comes next year potentially with Intel Xe onboard graphics. This might address GPU grunt and compute for the mini or allow extra cooling for the iMac.
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Something is going on with the 27" iMac. Best Buy shows "Sold Out" on their website for all stock models. Other sites are also showing out of stock.
And the Apple store now shows out of stock with earliest receive date of May 27th for all models.
Sure smells like something new is coming. Please have standard SSDs!
Third party retailers may be the better source for information at this time as it shows the retail channel is emptying but obviously a pinch of salt is required in this
Assuming no basic supply chain issues then Apple may well have been waiting for the channel to empty out a bit before dropping the iMac - possibly another reason why WWDC has been put back to late June.
The main Apple Store is showing pretty quick availability for 21.5" models while 27" models are weeks away.