Hey dude, I went there briefly in 2014. It's a weird city, that didn't leave me with a great impression, but I'd be willing to give it another chance sometime. Since you have a lot of time I'm sure you'll enjoy it more.
I made a little map. Let me know if you can't access it.
https://drive.google.com/open?id=1s8t0CAk3xdsouXMZNvTUFks9sDY&usp=sharingThe best things we did were getting a drink on the top floor of Pudong Shangri-La hotel at night overlooking the bund. A beer is pretty much USA city prices at that hotel but it's worth it. You have to get dumplings on Huanghe Road on the north edge of People's park. It's the completely opposite side from the Love Park spot but if you stay to the east side of the park you will find some funs spots. Eddie Huang goes there on his old Vice show if you want to watch that when it was still called Fresh off the Boat. That was the best thing I put in my mouth in that city. For other food go to the basement of a large department store/mall and you can't go wrong with delicious, cheap food.
As for skating, you must go to the Luding Bridge Spot in west Shanghai. It's ledge heaven, albeit a decent track from downtown.
In general, the tourist spots were underwhelming, so I'd suggest you do a day trip or two to see real Chinese historical sites and not the fabricated recently built "Old Town stuff" you find in Shanghai. There are many greats cities within reach from Shanghai to get a more....authentic experience.