I too am impressed by the way you are handling the whole situation so far.
And here's a thought that passed through my mind that I might mention because no one has brought it up yet.
Vulnerability can be a dangerous trap for caring people (which you obviously are). It's something I've seen, something I've been victim of and something I have to be on the watch for.
When someone we care for - at most any level - even just acquaintances, is going through tough times our instinct is to try to help if we can.
You add just a splash of 'potential' (or maybe real) attraction to that mix and all sorts of ideas start blasting off. And usually most of them are well intentioned.
But somehow our own desires get tangled up with their 'needs' and first thing you know there's no telling which is which.
And there is where it get's cloudy and mistakes get made.
I wish I had some solid advice to offer - but really I don't other than.....
"Be careful - go slow and try not to let fantasy overshadow reality"
As others have nicely mentioned, the seeds of drama and heartbreak are plentiful here.
And yet so are the seeds of something beautiful.
Which way it falls is probably going to require ....as we say...calling a spade a spade when it is one. And sometimes that's NOT going to be what someone wants to hear. And THAT will become somewhat a test of the viability of this and the people involved.
I hope for you all that it all comes up 'roses'.