With the exception that @ucbalumnus pointed out (trying to increase scores for automatic-for-stats $), I think that taking the test repeatedly might indicate personality issues: score grubbing, perfectionism, gaming tendencies (i.e., trying to raise one part of the SAT per test sitting), etc.
I would expect schools to pay attention to this. Everyone has an occasional bad test day, and you can’t read anything into a retest. A retest, not 7 retests. Someone retaking a test that is already above 2300 is, IMO, exhibiting behavior not indicative of good academic values.
There is, I believe, not a school or future employer who would reject an applicant solely because they got a 2300. If they exist, you don’t want to attend/work there anyway.
Re cost: I think ACT charges for each test date transmission, but SAT doesn’t.