While relatively weak fighters, Rogues can more than make up for their lack of direct combat ability with their deadly traps ... and frankly, they possess more Skills than any other Path. Hunting effectively with a Rogue requires a great deal of practice and coordination, both by the Rogue and by his fellow party members. It will likely, many times anyway, be a solitary venture for a Rogue, while nearly everything else they do is better done with company. If your Student enjoys company, but doesn't mind solitude either, this may be the Path for him.
Dexterity is easily the most important attribute for a Rogue, as nearly all of his Skills will require it. Intelligence is important, too, in order to learn certain Lore skills; brainy Rogues are said to be better at Higgling, too. No single attribute should be ignored, though, since your Student will be using them all. Your student will have to make some important decisions early on regarding his attribute allocation: Does he wish to be more effective in combat, while putting off learning some valuable non-combat skills? Or would he rather work towards learning non-combat skills like Tailoring and Gem Polishing? Note that the two are not mutually exclusive, but that at later insights, learning a more powerful trap may mean waiting to learn a Lore skill, or vice-versa. At first, they should probably distribute their attributes so that they can learn their first two traps from Daith: Needle Trap and Stilletto Trap.
Male Rogues have two options for their first-circle armor: both Jilt, the Piet Higgler, and Huberto, the Rucesion Tailor, sell Scout Leather. Huberto also sells the female's first-circle armor, the Cotte. For their second-circle armor, male Rogues need to return to Jilt to purchase Scout Leather, while females can buy their Brigandine from Steinar, the Abel armorer.
During their first circle, Rogues may want to stick with a Dirk or a stout Loures Saber for up-close fighting, as they need to build their Assail levels in order to have access to certain skills. Barring that, Daggers are available in Loures, while deadly Secrets can be purchased in Suomi. It may be best to wait to buy these until your Student learns the skill Throw Surigam from Keallach. though.
Also, in order successfully use the skill Lockpicking, Rogues will need a set of Lockpicks, available at any Rogue Trainer ... at a very hefty price, I might add. This may be one piece of equipment you want to purchase for them: 5,000 coins can be out of the reach of many young Aislings.
The first Skills and Secrets a Rogue should learn are available in Mileth, from the Rogue Trainer, and should be learned as quickly as possible. The first is Needle Trap, the first of a Rogue's trap Secret; the other is Lockpicking, needed, in conjunction with a set of Lockpicks, to open the chests in the Crypt.
Beyond these, it is difficult to say where your Student should go next. Certainly their next goal should be to learn Stilleto Trap, for which they will need a Good Snow Secret, but beyond that, there are so many choices for a Rogue that it is difficult to say which is most important. It is, largely, a matter of personal choice. Nearly every Mundane has something to teach to a Rogue, from confusion Secrets taught by Dark Wizards, to combat Skills taught by Fighter Trainers, to Lore Skills and Trap Secrets taught by Rogue Trainers. Even Armorers and Weapon Smiths can teach your Student skills. Taliesin's A Rogue's Pocket Guide to Skills and Secrets is an excellent reference, and should be used by your Student to determine which skills he desires most, so he can start planning to learn them right away.
Certain Skills, though, a Rogue is born knowing: he doesn't need to learn them, he just needs to practice them. The first of these is Higgling, which can be performed at any Higgler's. Higgling is basically what is referred to as a "short con", or confidence game. For 500 coins, a Higgler will allow your Student access to his overstock room, ostensibly to take 500 coins worth of overstocked goods off the Higgler's hands. With enough skill, though, by distracting the Higgler, he can make off with goods worth well more than 500 coins. In fact, with an Assistant to help distract the Higgler, he can make of with several thousand coins' worth of goods. One of the items your student will have access to in this way is Wine, and it is probably a good idea for him to stock up on that in order to trade it to Monks and Priests for personaca deum, a poison-curing potion that can come in handy when attempting to plunder the chests of the Crypt.
When he reaches his eleventh insight, your Student can begin practicing two new skills that he is not required to learn: Gem Polishing and Blade Smithing. Gem Polishing can be done at Jilt's in Piet; he need only have an unfinished gem of some sort, and pay the 500 coin "deposit" to use Jilt's tools. Jilt can also teach your Student the Gem Polishing Secret, which allows him to practice this skill in any non-Mundane area. As with most other Skills, when this one is performed with an Assistant, the chances of success are greater, and the chances of critical failure are lessened. When your Student acheives a certain amount of stature with the Skill, he can even attempt to Smith Rings at any Armorer's shop.
Blade Smithing, likewise, is done at any Weapon Smith's shop, and as with Jilt, a 500 coin "deposit" is required in order to use the forge. Unlike with Gem Polishing though, not just other Rogues, but even Warriors can Assist with Blade Smithing. In order to Smith a Sword or Soori, a Rogue must be four insights greater than is required to wield it; thus to Smith a Loures Saber, which can be used at the seventh insight, a Rogue must be of the eleventh insight. The Rogues I questioned seemed to be divided on which factor was more important in determining success, the Assistant's skill at Blade Smithing, or the Assistant's insight. But a story relayed to me by one may prove illustrative: at his eleventh insight, he went to Suomi to attempt to craft a Good Snow Secret so that he could learn Stilleto Trap, and asked a passing ninety-seventh insight Warrior to Assist him. She did so, perhaps too well: he crafted three Fine Snow Secrets before finally getting a Good one on his fourth try.
Rather than approaching their prey head-on, Rogues are crafty, cautious hunters, laying traps and taunting enemies into falling for them. Most Rogues I know are solitary hunters, but occasionally one is able to join a group and integrate his tactics with theirs. To do so requires great skill on all sides, as the entire party must work together to draw their prey across the Rogue's traps; alternatively, a Rogue can stand back and Throw Surigams at the prey while the Warriors and Monks in the party cover the front lines. One of the Rogue's most underused assets is his enhanced visual capabilities; by taking an overhead view of his current location ((Tab key)), a Rogue can see much farther than other Aislings, an especially important ability when the party needs a rest, and needs to be guided away from potentially hostile creatures.
Still, finding mixed-Path parties that are able to effectively utilize all of a Rogue's Skillsare rare, and your Student may have to get used to the fact that he will likely need to rely on his own Skills and cunning to survive. On the other hand, Rogues have so many options available to them, that there are many that simply do not engage in combat at all, instead preferring to practice their Smithing, Polishing, and Tailoring skills. And once they learn the Secret Hide, taught by the Rogue Trainer in Suomi, Rogues can attempt to plunder treasure chests in relative safety, without having to confront hostile creatures at all.
As solitary as they are on the battlefield, Rogues tend to be the most gregarious of all Paths. Much of their work requires Assistance, so they will often find themselves asking fellow Rogues, as well as Warriors and Monks, to lend a hand. Their Skills require a great deal of Labor, so they can often be found exchanging favor with Warriors, who have Labor to give, perhaps by Smithing a Blade for them. Encourage your Student to offer his Skills in trade for the things he needs, rather than merely asking for them; he's more likely to get a positive response, and will be able to practice his Skills at the same time.