A Form 1099-R for the distribution from the originating Roth IRA will have code J if you are under age 59½, code T if you are over age 59½ and the account is less than 5 years old, otherwise code Q. The subsequent rollover of that distribution is indicated on your tax return with the word ROLLOVER next to line 4b of Form 1040 and will be reported by the receiving Roth IRA as a rollover contribution in box 2 of Form 5498. Such rollovers are subject to the one-rollover-per-12-months limitation.
If done within a particular custodian or directly between custodians, the movement from one Roth IRA to another should have been done by a nonreportable trustee-to-trustee transfer with no reporting on Form 1099-R, Form 5498 or your tax return. Such nonreportable trustee-to-trustee transfers are not subject to any limitations on the frequency of such transfers because they are neither a distribution nor a rollover.
The fact that the receiving Roth IRA is a Roth IRA annuity has no bearing on the reporting.
The IRS does not require the IRA/SEP/SIMPLE box to be marked for distributions from a Roth IRA so Roth IRA custodians never mark this box when code J, T or Q is present in box 7.
