Property tax - I submitted my property tax to the city on 12/31/2016 (and received a receipt), but the City did not deduct the amount from my checking account until a few days later (in 2017). Which tax year should this be deducted from - 2016 or 2017?

2016 - The day you paid the tax and received a receipt (12/31/2016) is the day you can deduct the tax.  At that point you released the funds that they had an unrestricted right to receive regardless of when they cashed the check or debited your bank account.

Use the property taxes on your 2016 itemized deductions.