So every transaction you mean. You want the wallet to warn you to backup after every single send?
It does but it doesn't allow the keypool to run out. It adds a new key to the keypool everytime one is used.
Imagine a wallet has a keypool which contains 100 address. We will number them 1 to 100.
So:
Active Addresses: None
Keypool: 1 ... 100
If you took a backup right now you will notice you have all the addresses backed up to #100.
You need a new address. The wallet pulls the oldest key from the keypool "1". It immediately add a NEW key to the keypool lets call that 101.
Active Addresses: 1
Keypool: 2 ... 101
Next address used
Active Addresses: 1, 2
Keypool: 3 ... 102
48 more addresses used.
Active Addresses: 1, 2 .... 50
Keypool: 51 ... 150
50 more addresses used
Active Addresses: 1, 2 .... 100
Keypool: 101 ... 200
If you used another address it wouldn't be included in your backup.