That should work except the "Activation" will include those that are "Upgrading" to the plan for the first time, which should be fine if you allow the free trial to work on upgrades as well or don't allow upgrades tot he plan at all.
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When someone is PRO and expires they'll stay in PRO, but simply be expired. If they had a previous plan (your NORMAL USER plan for example) that is still active (could be lifetime, etc..) then they will revert back to it. I don't quite understand the problem. Simply have 2 plans, 1 frontend, 1 backend, add users to the backend plan whenever needed; nothing more you need to do.
Remove your free trial plan, then add a initial price and duration to the 3 month plan as well as the 1 year plan. When a user is disabled they simply renew to the paid duration of 3 months or 1 year (whichever they picked initially).
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