Customer (I Believe) trying to game us, looking for advice

There is a customer that has done a series of very shady things culminating in this current situation which I'm not sure the best way to handle.

First, the customer's grammar in communication is almost illegible. Not only illegible but written with no coherent message. I understand that not everyone has a high school level education, but it seems intentional to obscure whats being asked.

This person contacted our company (e-commerce site) about 10-12 times via our contact us form, which I take the time to respond to every message. His first 4-6 (is kind of blurry because he would send the same message multiple times changing 1-2 words or sentences). Only ever asked for us to give him free products. These are the only kind of messages I ignore.

So no response from me.

Then I received a series of contacts from the same email, written in the same matter, but claiming to be his kids and "wanting to help their daddy" and to give him something.

Again ignored

Then he made a purchase of $8 to an add-on of one of our products.

We filled it

Then a few days later received an email asking why he didn't receive the product ($80 value). I responded with the information of his purchase and why he received what he received. He then asked for us to cut him a deal on getting the rest of the product. We politely told him we could refund him if he sent back the add-on products.

he did not send them back

Then we had a sale (our biggest sale of the year on Father's day *this is when his "kids" contacted us). He bought 2 products separately in the sale, one on back order and one we shipped the next day). He contacted us 3-4 times about the back ordered item asking why it wasn't shipped together and such. We responded to him each time letting him know it was back-ordered and we would happily cancel the order if he preferred.

Finally, we shipped the back ordered item to him. We received an email from him a few days later asking if we had played a joke on him and where his package was (then wrote about 4 paragraphs on wanting another sticker because his kid put it on the refrigerator). he then sent a picture of a package that had a small hole in the bottom and asked if the product could have fallen out. The package had clearly been opened from the other end already and the hole was not nearly large enough for the content to fall out.

He also chose it to be shipped First Class USPS (which you cannot file a claim for) (we removed this shipping option already)

Long story, question is WTF and am i crazy? If this was someone who seemed legit I would do my best to help resolve the situation. The product he purchased is about $100. It wouldn't break us to send it to him, but I don't feel that should be my solution. Looking for input on the best way to handle this for this and future situations.

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