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Your mercantile skill goes up a little bit every time you sell (not buy) something. Selling stuff in a batch is the same as selling one of the thing. So, wander around the Imperial City and pick as many Fly Amanitas and Sacred Lotuses as you can find (there are lots of Fly Amanitas in the graveyards around the tower in the centre of the city and lots of Sacred Lotuses in the moat surrounding the wall around the inner city), then take them to an alchemy merchant and sell them, one by one. Or collect iron arrows from dungeon crawls and sell them, one by one.

Mercantile training can be had from the following people.

Foroch (basic) Inn west of Kvatch,

Mach-Na (basic) Her bookstore in Cheydinhal,

Margate (advanced) East of the Great Chapel in Leyawiin,

Seed-Neeus (advanced) Northern Goods and Trade in Chorrol,

Palonirya (master) Divine Elegance in the Imperial City Market District.

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Q: How do you increase mercantile skill in oblivion?
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