• The transaction is older than 180 days.

These transactions are from July of this year. 

• The dollar amount in QuickBooks is different than what cleared the bank.

All three dollar amounts show the exact same amount. 

• The transaction type is different in QuickBooks than at the bank. QuickBooks wants to match a check with a check and an expense with an ACH or debit/credit card swipe.

The Paypal Bank shows it as a transfer from  a bank account, and the checking account Just shows "PayPal" in the description and payee, but the memo includes  "DES:INST XFER". Not sure if that answers your question. 

• The transaction was recorded in a different bank account.

These transactions only show up in my checking account, paypal bank account, and paypal credit account. So they are where they are supposed to be. 

• The transaction from the bank is a payment/ deposit of two or more open transactions in QuickBooks.

Nope, same amount, across the board. 

If everything is correct, let's match the transactions on an incognito window.
Incognito didn't work either. QBO still can't find the transaction. Two things of note: 

1. I pay bills every two weeks. So the transfer for pay period 1 keeps trying to match to the transfer from pay period 2 which is two weeks later. So they CAN match, just not to the correct one. 

2. When I change the date in the register through the Chart of Accounts, the date stays as the updated date. BUT if you go into the Banking tab to the same account and go into the "Categorized" list of transaction, the original, earlier date, still displays - it doesnt show the updated date.