While it took until the 15th to get all the rent, it gave her tremendous peace of mind knowing the rent was being paid each month without her involvement, and I felt better knowing I was guaranteed to get the rent without excuses, stress or late fees.Mark, you win the Good Human Of The Day Award!

Has anyone figured out how to vote a post down...maybe give some sheep awards for unnecessarily giving kudos...anyway...it's all relative.

If you can't prove it with evidence, the judge isn't going to just award you his money because it's an not in pristine condition. 

As well, I do not believe you will need to lawyer up, because if you prevail in court, I suspect the judge will just award you treble damages, but check your local laws online to be sure. 

A "professional" tenant can tie you up in court for the best part of a year, especially if you make even a tiny procedural mistake.Chapter 93A (the Consumer Protection Act) also applies to landlords and can award a plaintiff up to 3 X damages.

Applying other's asset allocation to your life is like trying to take an award winning chili recipe and make tacos.

It did go to court , she lost and since the contractor had a great contract  he was awarded damages .

In the end they provided him with terrible quality work and the building was  discovered by the buyer/owners to have many defects and sued the seller in court and won a $1,750,000.00 award from the court.

But all the courts can award is a judgement. 

They are biased WILDLY in favor of the tenant, and if you screw up, they can sue and be awarded triple damages.