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Theft of personal property

My dog sitter stole various personal items (women's shoes, a suitcase, and other minor articles). It was recently discovered that 20 pairs of my son's collectible Nike and Air Jordan shoes were stolen. He has been collecting these for over 10 years. The current market value of his stolen items is around $4900. The boxes were emptied and replaced on the shelves. I only discovered them missing when I cleaned the closet. I have contacted the police. 

Further details:

The dog sitter was hired through a licensed and bonded dog-sitting service.

The theft occurred in July of 2019. This is when I discovered my personal stolen items (women's shoes, etc.) . The service reimbursed me for these items.

Witnesses: I returned home around 11am from my trip and noticed her car was in the driveway. I said to my boyfriend and mother that it was strange the sitter was still here. She should have been gone early morning. As we were getting out of the car, she comes out of the house with a white trash bag. It was obvious there were items in the bag. We startled her. She said that she didn't have a suitcase. (referring to the reason she had a trash bag). The next day I discovered my shoes missing and over the course of the next 2 weeks the other items as well. (Again, I have been reimbursed for these).

July 2020

I started to clean out the closet in my son's room to bring him his remaining clothes and shoes. It was only then I had discovered the shoes were missing.  He has Paypal receipts for of the shoes (Paypay only goes back to 2017). We have the original boxes with prices on the labels. These items have grown in value. In researching online for some recent sales of the same shoes, some are valued now up to $500.   

What I need answers to:

1. After the police report has been completed. what are the next steps? What is the procedure on the part of the police in this case?

2. I want to serve the dog sitting company notice that they owe money for these stolen shoes. Should I have legal papers served (pay or we go to court) or, should I first call them to see if they are willing to pay?

3. I want to prosecute the dog sitter. Would it be advisable to wait until after I settle with the dog sitting service? I did not physically see the shoes in her possession, but would probable cause come into play knowing the events I outlined above?

4. Would probable cause be enough to issue a warrant to search her apartment? 

5. Should I see if her bank accounts, phone and computer records can be seized to see if she sold any of these items online?

6. Finally, I don't know what I do't know, so is there anything else I need to be aware of?

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