Start the process so the red tape is removed if it becomes necessary to remove the tenant. When they start trying to bully or get manipulative, they lose any flexibility with me. “never had a landlord do that to her before” sounds like an attempt (conscious or subconscious) to bully and make you feel like you are the only landlord who would charge them because you are so heartless. You can avoid the issue here the most by setting better procedural rules for tenant screening/on-boarding (that's a post for another day) and procedural rules for tenant removal.
My rules, which vary significantly depending on what state the property is in, give the 5 day grace period before late fees on rent. A set number of days after that they are attempted to be contacted by phone, email/software, and text etc. A set number of days given the notice to quit/cure. A set number of days later they get next step and so on and so on. Learn your states law, then build your own written procedure and schedule. Make the schedule and steps so simple, direct, straightforward, and automated that a 12 year old could easily run your management system.
Except for the 5 day grace period and late fee, I don't publish this schedule in the lease agreement so they don't game the system. It is, however, in the manual I wrote for the managers. My only exception to the rules and procedures for my tenants is that I allow 2 months of no fees and allow them to break the lease if the primary income earner on the lease dies and they let me know they can't pay rent. I've never had that happen so far. Every other tenant situation is still bound by contract to pay rent.
I would suggest setting up a system like this. Decide where the line needs to be drawn ahead of time. Once you have rules, you can take your emotions out of the equation. You don't have to spend emotional capital and subject yourself to bullying every time someone wants to be an exception to the commitment they made.
So many managers are terrible managers because they never took the simple step of deciding what the rule was ahead of time when nobody was pressuring them. They get burnt out repeatedly making judgement calls where they continually try to emotionally connect with the tenant's situation to decide where to draw the line when instead, they could have made the decision once without any pressure on them.