I thnk your problem arose from the common area of a variety of awarenesses, not to say competencies, in some units. Any ATCO worth the name should know that, if you are given a 'when ready, to expect' clearance, then they cannot expect you to make that if they then level you off at an intermediate level. To help them, you should certainly pipe up and let them know it's impossible, as it will add to their learning!
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What "guidelines" do ATCOs work to over descent distances required? Do they take into account the wind e.g. tailwind?
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Many of us know the usual TOD points for a given cruise level to make a restriction, and will give descent instructions to allow this to happen. Sometimes we can get distracted or involved in other tasks, and may leave it late. If that's the case, we much appreciate your help in complying, unless the Stuka dive will upset the pax! But if it's impossible, say so and we will take the necessary action.
I must also confess that the strong easterlies at altitude recently have caught me out occasionally and I was happy to try to coordinate a different profile with the next sector when told that the restriction was unachievable. I'm afraid some people do it by numbers, however...
As a counter comment, can I outline the pointlessness of saying 'Request Descent', receiving a clearance and then just sitting there for another 15nm or, worse, saying "Is that when ready?". I know you want to set the level in the MCP and allow the aircraft to follow the VNAV path, but we have probably amended our plan to allow you to descend when you asked for it, and if you do not, you mess up the plan. So in the same way as some ATCOs do it by numbers, some pilots behave as computer operators and not pilots.
If you ask for descent, descend as soon as you receive the clearance!!