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Being fair, honest, understanding, and patient is the best policy for tenant and landlord alike, but there are those greedy/neurotic people to deal with.
Meet with your tenant before and give them the grill first to see how they really respond. Who knows, the appartment could have been rented already.
State boldly in the least that month to month after lease expiration is not an option(state law may have precidence over this though). Document with video every fixture/wall/carpet beforehand so there's no question of reasonable wear-and-tear.
Fix everything that needs to be fixed, this will not only give peace of mind but is deductable and increases property value.
Talk to them on the phone every 3 months to see how everything is going, and view the appartment a month before lease expires.
Work with them and be flexable within reason.
In your case, I'd get a restraining order, send a bill for yor time, give 24 hours notice and then document the decrepid state she's kept the place in. Find out where she works, report undocumented income to the IRS, and sue to recover your attorneys fees. Play her game better than her if it's worth it per hour. Be nice to all the nice people, the others....
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Meanwhile other things are still happening.
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