His family had lost a son and a daughter now.
( ( His family ) ( ( had ( ( lost ( ( ( a son ) and ) ( a daughter ) ) ) now ) ) . ) )
(ROOT (S (NP (PRP$ His) (NN family)) (VP (VBD had) (VP (VBN lost) (NP (NP (DT a) (NN son)) (CC and) (NP (DT a) (NN daughter))) (ADVP (RB now)))) (. .)))
The family had children that have passed away.
( ( The family ) ( ( had ( children ( that ( have ( passed away ) ) ) ) ) . ) )
(ROOT (S (NP (DT The) (NN family)) (VP (VBD had) (NP (NP (NNS children)) (SBAR (WHNP (WDT that)) (S (VP (VBP have) (VP (VBN passed) (PRT (RP away)))))))) (. .)))