When you have NODELAY=false (which is the default), when you call send() with less bytes than the TCP window, the bytes are not really sent immediately, so you're right. The OS will wait a little to see if you call another send(), in order to use only one packet to transmit the combined data, and avoid wasting a TCP header.
When NODELAY=true the data is transmitted when you call send(), so you can (theoretically) count on the returned value. But this is not recommended due to the added network inefficiency.
All in all, if you don't need absolute precision, you can use the value returned by send() even when NODELAY=true. The value will not reflect immediate reality, but some miliseconds later it will (but also check for lost connections, since the last data block you sent could have been lost). Once the connection is gracefully terminated, you can trust all the data was transmitted. If it wasn't, you'll know before - either because the connection was abruptly dropped or because you received a data retention related error (or any other).