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The Elder Scrolls IV: Oblivion Hints
Interpersonal Skills
1 of 5: Speechcraft is really easy to practice. Just talk to someone who isn't a shopkeeper and play the disposition mini-game over and over.
2 of 5: Each time, rapidly choose "wedges" at random instead of taking the time to figure out the best strategy. The person's disposition will probably end up going down, but your Speechcraft skill will go up, and that's what matters.
3 of 5: Unfortunately, Mercantile is one of the most tedious skills of all to practice. The way to do it is sell a large quantity of cheap items (like iron arrows) to a shopkeeper one at a time, then buy them back one at a time, and so on.
4 of 5: You can get a free +5 to Mercantile by completing the Chorrol misc. quest "A Shadow Over Hackdirt," so it's best to put off finishing that quest until your Mercantile is 95. Those last five points would be the hardest to practice normally. (You might also want to use training a few times right before reaching 95.)
5 of 5: It's worth it to get your Mercantile skill up to 100 as early as you can. Not only will all shops have 500 more gold to spend, but there's a secret, undocumented effect that causes every merchant to always buy and sell items at their base value no matter what the haggle setting is. (Though note that they still can't give you more gold for an item than they have.)