At the end of my quest I want to give the player a reward but if the alias does not have enough gold they will give the player a random item suited to their character.

I have a Flower quest alias and a Bug quest alias for the children to give as rewards.

The Flower quest alias - find matching reference - conditions - haskeyword 'GiftFlower' == 1 AND

But it won't fill the alias. I have no idea why. Either I've missed something, or its simply not finding the alias within the area (On wiki it says 'find matching reference' will only find aliases in the loaded area unless they are specific or unique).

The longwinded approach would be to create every possible gift within the Actor Alias' inventory and use a script to choose one to give to the player. But I was hoping for an easier way. Or I need to rethink.

Have you placed gift flowers in the area, that could be found?

You could use the "Create Reference to Object" fill type to create a new reference of a base object (flower, etc.) and have it added to the inventory of the child alias.