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This may not be the most appropriate forum for your question. The separation you are using is done using the Custom CMYK engine, which is a legacy (pre-CM) mechanism in Photoshop that has no direct relationship to ICC color-managed workflows. Legacy questions may be better addressed to other forums.
On the other hand, if, rather than use the Custom CMYK engine, you wish to separate your grayscale image to a CMYK ICC profile appropriate to your output conditions, the procedures are clearly outlined in "Real World Color Management", by Bruce Fraser, Chris Murphy and Fred Bunting. (Look for it on the Amazon site.)
When the output conditions are not known, make sure to speak to the printers once they have been picked, and clearly communicate to them your concerns. You can provide a CMYK image file separated for US Web Coated (SWOP) v2, and ask them to reseparate it appropriately for their own press conditions. You could also provide the grayscale file, if they would rather have that one. In any case, make sure to tell them that you are looking for a high GCR.
It's also a good idea to send them a properly color-managed proof (aimed at US Web Coated (SWOP) v2), and tell them to make sure to match it. Other than that, and in the absence of any information that is more detailed and specific, there's not much else you can do.
>When I drop the photo into InDesign, the Prepress defaults strip the profile and convert to US Web Coated SWOP, BUT preserves the numbers. The photo takes on a cooler, more blueish tint. Is this to be expected?
converting the image. The North America Prepress 2 color presets use the "Preserve Numbers (Ignore Linked Profiles)" policy for CMYK. This policy
the CMYK profile embedded in the image and
the default CMYK profile instead. The image numbers are left untouched, but the appearance changes because the default profile (U.S. Web Coated (SWOP) v2) describes print conditions that differ from those established in your Custom CMYK profile.