TRS re-enrollment penalty

Such a rollover from a Roth IRA is not permitted, so this transaction can't be a rollover.  Once in a Roth IRA, the only rollover (or transfer) that is permitted is to another Roth IRA.  The only way that money can be moved from a Roth IRA to the TRS is if you took a reportable distribution from the Roth IRA and, once what you had was nothing but cash independent any retirement account, you used the cash to somehow buy back into the TRS, plan permitting.

I have no specific knowledge in this area, but my guess is that any fees associated with such a buy-back would not be deductible.