Lets break it down one by one.
1. Old Man: As a sorc' you don't need to get any food for the cat. Just some spell casting required in the right place
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×Approach the tree he climbs, when he's up in the branches cast Shadow and he'll come down
2. The Healer: He'll give you his support if you finish his romance series of quests. That requires a little back and forth between the two villages, some flowers, and paying a bridge toll. Most of those are covered in various other posts here.
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×You'll get the flowers by telling the female elf in the underground city about her lost friend - he's the pile of stones off to the western edge of the map and can be spoken to if you use the potion that was a reward for dealing with the Haugbui. The toll can be paid with money, a gemstone, the cursed ring, maybe something else?
3. The shopkeeper really respects her dead husbands opinion.
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×Haven't done it myself but the elf lady in the underground city trades a staff that lets you talk to the dead - her husband is buried in the mound over in the graveyard
4. One of the citizens is in the other town's jail - head over there and see what she wants for her support
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×You can bribe the jailkeeper to release her
5. The dark haired man will support you if you finish his quest
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×Bring him the chest that was invisible in the crystal room in the underground area - you'll find it by casting 6th sense and then clicking on the area if I'm remembering correctly
Think that covers it. You only need 4 - the easy ones were the person in prison, the healer, the librarian, and the dark haired man.
[Last edited by oneoff at 12-30-2013 10:17 AM]
) then the cat just jumps down from the tree for you without fish :3 ) 
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I haven't yet found something that he would accept in order to initiate the challenge, so I haven't been able to get a go at it. Thanks for the tip! ^^