TW-MACAU-SHANGHAI-MACAU-TW

Hi there! I'm having problems reaching the Chinese embassy as there is not one in Taiwan, and it's been difficult trying to reach the consuls in the US.

I'm a US citizen and currently live in Taiwan, and my itinerary is below:
Taiwan - Macau, stay overnight
Macau - Shanghai Pudong, stay for 2 days
Shanghai - Macau, stay overnight
Macau - Taiwan

My questions are:
1. Does this grant me a free transit in Shanghai? Not sure if Shanghai would see consider my inbound and outbound as from Macau.

2. IF Macau is considered a third region in my case, a Visa is not necessary, correct?

3. Do I need to apply for a free transit permit or anything of that sort at the Pudong airport in Shanghai?
Thanks so much for your time!! Really appreciate the help.
Michelle