My question is, would it be possible to sell my own items on my blog? I know there’s no store feature, but I could do it manually and bill people with paypal or something to that extent. So basically I would have pages with my products, and people could contact me and place their order on which item(s) they would like to purchase. Everything else would be handled through email and paypal. Would this comply with WordPress policies? Would I have to upgrade in order to do this? Or can I just use the free version? Also my products would be my own creations (e.g. paintings).
Yes you can sell your own creations but do be aware that WordPress.com blogs cannot be equiped for ecommerce. You can use a PayPal button and a contact form and that’s it. There is no shopping cart ability here.