Yep, the SRV record thing is tricky because you can't create two srv records in the same domain for _sipinternatls. There are a few ways to deal with it, though.
I think the easiest way is to just manually configure your OCS clients for ocspool.company.com:5061. This will keep you from needing a separate SRV record.
However, the best long-term solution is this: If you are using an LCS access proxy, you can replace it with an OCS edge server. Then you can configure your internal SRV records to point to the outside interface of the Edge server (sip.company.com) on port 443. This way LCS clients all point to the Edge & then the edge distributes the request to the LCS front end. The OCS clients also point at the edge & it distributes the requests to the OCS front end. This is the way I have things woking in our environment and it has been working very well.
And I also agree with your strategy on the user migration, that's probably the best way to do it.
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