Let's start with the map. The first objective involves meeting up with your taskmaster, who provides you with the laundry lists of loot that must be nicked in order for you to pass the test. His location is clearly marked on the map - but at first my position clearly wasn't. It too me a while to realize that my location is only roughly indicated by the grey color over the part of town that I'm currently in. What's worse, the map is facing the wrong way as North is Left, and there are no signposts or obvious waymarkers about until quite a ways later.
Then there's the part about getting to the meeting. The correct path is straight forward, but it's blocked by a portcullis. For plot reasons you don't start with your lockpicks (but you don't find that out until later) so you can't pick open the door right next to the portcullis, nor the portcullis itself. Time to look for another route. While scouting out an alternate path I noticed that all the streets are watched over by guards conveniently located standing up against a wall, under a strong light source, meaning they can't be snuck upon and dealt with. This is the prevalent theme for the entire FM, I counted close to 20 guards/Hammers doing precisely this.
Anyway, the 'correct' way past the portcullis is to get into the house on the left (the one with the locked door) via the second-floor window... the one with a convenient wooden windowsill in front of it... but is actually not a wooden windowsill, as your broken rope arrow will tell you. The 'correct' way to get through the 'correct way' is to shoot the rope at the wooden pole holding up the banner next to the windowsill. Once inside you can make your way through the house, to the kitchen and out the back to reach the other side of the portcullis. Mind the sleeping noble who instantly goes from 'asleep' to 'running to the guards' if he wakes up. Mind yet another guard standing up against the wall, under a strong light source, facing towards you. Your only saving grace is that you can turn off the light here, triggering the guard's script, as he saunters over to turn it back on, putting him within reach of your blackjack. Once you reach the portcullis from the other side, you'll notice that there's a lever right next to it, and it's frobbable from the other side.
Then there's the meeting. It's in a cul-de-sac, under a lit lamppost, up on a platform on the right-hand side. At the other end is an archer guard stationed up against a wall, underneath a strong light source. No, you can't get to the lamppost without alerting him. (Be grateful there are flashbombs available.) Once he's out of the way you realize that there's only a puddle of blood where your taskmaster should be, but there are scribblings present which point to a ledge above you and across the alley. This ledge is conveniently placed so that it looks like you could jump up and mantle it, but you can't. The 'correct' way to get up there is to keep looking up until you find the hard-to-spot wooden beam. The tricky part isn't hitting the beam with a rope arrow, nor is it the somewhat dodgy jump you'll have to make to reach that ledge. No, it's getting the rope arrow back without breaking your neck, because you will need it.
(Before continuing I have to touch on the readable that you find up there. It's from Drannor the taskmaster, telling you that he can't be there as he's been captured by the authorities (past tense). And yet, somehow, Drannor had time to be spotted and injured by the coppers, evade them, climb up here and stash the things you find here, then make the scribblings, then climb back down and be carted off to a hammer dungeon and find the time to write you a note. Unless he can predict the future or has access to a time machine, I'm seeing a gaping plothole here.)
ANYway, doing all that nets you a slew of new objectives waiting to be completed, and one lockpick. It's best to get the other lockpick first, which fortunately is located just a quick walk around the corner. Mind the floor which looks like reinforced stone, but is actually metal. Eventually you'll find yourself in Clickkey Yard. To the west is the locksmith's house, which is only marked so on the map. There are two ways inside (the locked front door is actually your exit) but both seem to involve acrobatics. You could fire a rope arrow into the beam high up and jump from there to either the upper story windows, or to the balcony. While this is the easy way in, it's also designed to cost you a rope arrow, as it's almost impossible to retrieve it without breaking your neck. If you enter via the balcony you will be greeted with a faceful of a guard standing right outside the room, right up against the wall, under a strong light source. (I hope you put that candle out.) At least this one turns on the spot sometimes, but he's still right in front of you. The 'correct' way to get into the locksmith's house is via the (unlocked) windows, except they open outwards, so you can't land on the ledge and open them. You can't reach the windows from the rope arrow, so what to do?
The 'correct' way to get to the 'correct way' into the locksmith's house is from the low roof on the house to the left of the locksmith, but to get there you need to climb up the pipes on the house across the yard - the one with the portcullis covering the front door, the second-floor balcony and the open window, through which you can hear (at least) one patrolling guard inside. BUT... once you climb up on the balcony and step in front of that open window, the unseen/unheard/unmoving archer guard on the ground floor of the building activates his script, opens the portcullis and starts patrolling Clickkey Yard... for no other reason than to send a 'Fuck You'-statement to the player. If you're thinking "that's OK, I don't need to step in front of that window anyway, you are Wrong. Did I forget to mention that the loot objective on Expert difficulty requires 99.34% of all loot found in the mission? Did I also forget to mention that you can't access a large part of the FM on Normal difficulty? Also, that metal pipe will make noise no matter what you do, so you might as well get in there and deal with the guards. Note the guard on the third floor (standing up against the wall, facing towards the stairs, under a strong light source) who's guarding absolutely nothing but his purse. Also note the totally empty basement.
ANYWAY, back to the locksmith. Assuming you've done all of the above and managed to get the drop on that guard inside, you now have access to the lower floor, where there are three doors. If you take the door on the right, you end up in the latrine underneath the stairs and may get trapped there by the architecture. The door on the left leads to an uninteresting storeroom, but the door forward leads to the shop itself. The back room has one torch acting as the sole light source, but even with that doused you're still lit up like a street lamp. And in the shop itself is a guard, standing up against the wall, under a strong light source, covering both exits, with your missing lockpick located behind him. Imagine my relief when I noticed that he turns around occasionally...