It's hard. But it can be very rewarding.
The best way to proceed is to be very straightforward about what you need to do a good job. You have to let them know, gently, that you can't paint what you can't see, and that making something up won't work or be believable. Also, reserve the right to bail if no suitable reference is available. You're not a magician, and you can't bring that person back, and with all of the emotion inherent in the situation, especially here, you can't afford the bad feeling that a bad job will incur. Sometimes, sadly, there is just nothing to work from, and it's hard to say no, but necessary.
I usually request at least one professionally taken head and shoulders photographic portrait, that's sharp and clear enough to give you what you need. Of course, all parties have to agree that that's the principle image on which to base the portrait. I sometimes bring this head to a model's body that I photograph, if I need more pose, but this has to be very carefully matched up with a believable angle and lighting. Don't put an inside head on a scene that's shot outside, for instance. Though someone has done it successfully in the past, I'm sure, it very rarely works.
Then I ask for a number of good "garden variety" snapshots of this person at the same age from many angles, to round out my understanding of them.
IF they have a comprehensive photo they took that's just perfect, with enough detail, and it's sharp and clear, you can work from that. This is more unusual than you might think. An amateurishly taken photo will result in an amateurish painting. Remember that in this situation, you are only as good as your reference.
I'd ask for the photos. You may not get adequate quality receiving them electronically. Make your own scans and do any doctoring from the hard copies.
Be very sensitive to their feelings, but don't let them talk you into something you can't provide. This situation seems extremely fresh and raw, so proceed with caution. Their mood may swing wildly through this process, and you need to feel them out slowly.
As I say, it can be extremely rewarding, but only if it goes just right.
Best--TE
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