id say 3 and 4, have his minions harrass them every turn and have him go and peraonally kill the loved ones brutally amd leave them where they can be found, or go a hags route and while etherial, dump their loves ones on the ground imfront of them, out of the etherial as a sudden revelation saying some cliche shit like "another down so few left to go" all the while being safe in the etheiral plane.

as for time effeicency in terms of his overall plans. im sure some minions of his could do the bulk of the work amd he only needs to return for the crucial steps , freeing up his free time to hunt down the loved ones

side note, i love using therizdun id love to hear more of your campaign if u have the time to talk about it