One part of that loophole was fixed. Re-applyiing the redshirt will never result in a better WE, than the previous application. If it went to 1, then it will go to 1 again the 2nd time through the n+1st time.
The loophole that you are attempting to exploit, holding him out and redshirting only after he's made some gains towards his potential, probably should be made a little less attractive at some point. Maybe add a risk of x'fer that doesn't now exist or increase the chance that an off-depth chart player will be subbed into a game in which injuries or fouls or both have left the team short handed. On the other hand, I wouldn't put that much priority on it.