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The Elder Scrolls V: Skyrim Game Add-Ons (DLC) Hints
What all should I have my steward purchase for me?
1 of 7: Say you'd like him to make some improvements to the house. That'll get you a list of animals you can buy and people you can buy the services of.
2 of 7: The carriage is the most useful one. You can ask the carriage driver to take you to a bunch of different places that the regular carriages at the stables don't go. That can be handy in discovering some new places (provided you haven't already discovered them all).
3 of 7: The bard is very expensive, and he won't even show up until after you finish building your main hall. All you can do with him is ask him to play various instruments and sing a few songs. Not really worth 1500 gold, in my opinion.
4 of 7: As for the animals, building a stable and then buying a horse can be handy if you don't already own a horse. The cow is just for "decoration," and the chickens will have a nest that you can raid periodically for chicken eggs. (Note that you can buy up to three chickens, but you'll still only get one nest in the animal pen.)
5 of 7: The other two categories of things you can have your steward buy are building materials and furnishings for the house.
6 of 7: Neither one is really useful. You can get all the clay and quarried stone you want by using a pickaxe on the nearby clay deposits and stone quarry. It can be convenient to have your steward buy sawn logs for you, since that'll keep you from having to make extra trips to sawmills when you run low.
7 of 7: As for having him buy furnishings for the house, that's just an expensive (and lazy) way to furnish each section of the manor that you've finished building. It's much cheaper to find and/or buy all the materials you need and use the workbenches inside the house to put in the furnishings yourself (especially if you want to pick and choose).