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"He can't start getting to the bigger prize if the cloture motion passes."

Unfortunately, I think you are laying out the roadmap for Dem victory. By the rules of engagement (ROE) Frist has defined, he is not "allowed" to call for a rules change vote until the Dems block cloture. Hence, the Dems can repeat the current drama as many times as they want to, until the Repub coaliton hits a weak spot.

In other words, Frist has given tne Dems the choice of when the critical battle will take place. This ensures they will win. Or am I missing something?

By the rules of engagement (ROE) Frist has defined, he is not "allowed" to call for a rules change vote until the Dems block cloture. Hence, the Dems can repeat the current drama as many times as they want to, until the Repub coaliton hits a weak spot.

In other words, Frist has given tne Dems the choice of when the critical battle will take place. This ensures they will win.

There are always a number of optional approaches, and within each appraoch, there are a number of aveneues the drama can play out. In order to restore a simple majority requirement to reject presidential nominees, I see at least three broad options:

Move directly to change Rule XXII (unlikely - takes 2/3rds). This option could be introduced at any time. It does not require a nominee, or need to work in the context of consideration of a nomination.
The path we are on - bring a nominee, ask for the vote, and file a cloture motion in reaction to an objection to take the vote.
Confront the propriety of using cloture at all, in the context of nominations. I advocate this as a matter of principle, and Senate practice has a clear example for this where it handles treaties. The same arguments that I prefer can also come up in the context of cloture.

In the second option, you are right that the timing of the battle is driven by the failure to obtain cloture. This outcome is almost certainly in DEM hands. In a system of unanimous consent, the minority has the nuclear trigger.

What will the DEMs win if cloture passes? Only the retention of the same power they have today, and only at the expense of voting on Owen.