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Thought is it may give him incumbent advantage.
He can't be the incumbent.
The race for McConnell's seat is already underway and the Republican nominee already picked. Additionally all other deadlines to run as an Independent have passed.
Ok rereading this I think you missed the whole shenanigan the last few weeks. If McConnell is declared dead before Aug 3, then there is a special election/appointment (because that's debated). If McConnell is declared dead on or after Aug 3, then there is a rule that kicks in that because it's only 3 months until the midterms, then there is no special election/appointment and McConnell's seat election gets rolled up together with the midterms.
The GOP is concerned that if McConnell is declared dead before Aug 3, then there will be an appointment/special election to replace McConnell before the midterms. That will make Massie/whoever wins/is appointed the "incumbent". Yes that will be short lived because the midterm election will happen anyway. But they still don't want it. Their thought process is that if Massie wins/is appointed, then it will give him an "incumbent" advantage in the midterms (in scare quotes if you want). So they are keeping McConnell on life support until Aug 3 so that it gets punted to the mdterms.
So I don't think I've missed it.
As you said,
But I don't believe Massie can run in the midterms.
I admit I am wrong that he can't be the incumbent, because technically being the incumbent just implies holding the office, not running for the office they currently hold, but in a world where a special election happens (or an appointment), and Massie takes McConnell's Senate seat, he can not run in the midterm election.
Per Ballotpedia the deadline to file as a unaffiliated (independent) was in June.
Any special election would only cover the remainder of McConnell's term and not the term after, which is a whole separate election that is happening in November.
My guess, after reading more about it, would be that a special election could include the two current midterm candidates AND Massie (as an independent), and that election could result in a Democrat winning. Then because the Democrats "just won" it would lower Republican voter turnout in the midterms. (Although I suspect in this scenario the midterm and special election would both take place in November, so it wouldn't be two separate elections, but Massie would get more air time to ensure the Republican doesn't win.)