This plotline may cost you the most money, between the contacts, the equipment, and all the rides from Sharkey. Besides that, though, there's not a lot of action. With the exception of the prison escape, this plotline is basically just running from one place to another.
Go to Icarus Descending and talk to Caleb Brightmore. (2)[edit]
Icarus Descending has some restrictions (6+ Reputation or an Elf in your party) on letting you in, but they only apply before you ask Boris about Michael at the very beginning of the game. So, as long as you've done that, you should be able to go in. Take a cab to the Renraku Arcology and go left to the next section of the city when you get there. You'll now be in Downtown Seattle, right in front of Icarus Descending. Enter and move to the back booth to meet Caleb. He'll tell you about your brother's last shadowrun and give you some info on Frosty, the elf who was partly behind the run. Caleb says she hangs out in the Tarislar City Inn in the Puyallup Barrens, the same place that you found Tabatha Shale in at the very beginning of the game.
Go to the Tarislar City Inn and ask about Frosty.[edit]
Go back to the Tarislar City Inn, this time asking the man there about Frosty. He'll tell you that she joined the elves of the Sinsearach.
Go to Sinsearach, speak to the elders, and agree to be tested.[edit]
As the guy at the Tarislar City Inn tells you, the Sinsearach is a part of the Salish-Shidhe wilderness. If you've been there before, great. If you don't know how to get to the Salish-Shidhe, read Step 1 of the "David Owlfeather" entry in Part 2b of this section. That'll explain it in much greater detail, but basically you can either get a passport or have Sharkey drop you off. If you choose the latter, just save up an extra 2 grand and have her drop you right at the Sinsearach's front door. If you are forced to start out from the beginning of the Salish-Shidhe by the highway, though, I'll tell you how to get there.
Before I do, though, you should know that you need some decent equipment if you expect to survive in the wilderness. It helps to have an extra runner or two, and all characters should have at least an Armor Jacket, but preferably some Combat Armor. Get Predators (or strong magic) all around and bring plenty of ammo and Medkits. If you're still going down to the demons that live out there, I suggest upgrading your characters' defense-related attributes through cyberware and/or Karma. And finally, I suggest you make contact with Sharkey before going and bringing along an extra 10 or 11 grand. This will let you skip the walking and just be flown back and forth to where you need to be.
From the highway, walk southeast around the logs and trees and you'll find a bridge leading east. Cross it and you'll be in the AmerIndian village. Go to the far southeast corner of the village and enter the cave at the opening. Once inside, follow the cave wall down and then to the right. You'll come to an exit which you should take. You'll be outdoors again. Move to your southwest until you find another cave entrance in the western edge of the map. Go in and follow the wall down and left until you come to another exit. This will take you to another cavern, where you should walk a little bit down-left until you see another exit. Take this and you'll be in a third cavern. Walk down-left and keep following the wall as it goes left until you see the final exit in the bottom wall. Take it and you'll once again be outside.
From here, follow the dirt path south until you reach the first bridge. Cross the bridge and continue following the path. You'll see an upward branch, then a downward branch, then another upward branch. Take that one upward and keep following the path until you get to the Sinsearach gates. When you get there, go ahead and enter. You can ask the elf at the gate about Caleb Brightmore and Frosty, but you won't get much useful information. When you ask him to see the elders, though, he'll show you in to see Lady Gillian and the rest of the elders.
After you ask Gillian about Frosty, she'll say that you have to be tested before she'll help you. What is it with people and tests in this game? Doesn't anybody take people at their word any more? I guess not. Anyway, say "yes" when she asks you if you are willing to be tested. The first part is simply to deliver a package to Red Buffalo Woman who lives in the AmerIndian village.
Go to Red Buffalo Woman.[edit]
After you speak with Gillian, the guard will offer to fly you back to the highway for 1,000¥. You brought that extra cash, right? If you did, take the ride and head back southeast from where he drops you off to get to the village. If you don't have the money, you'll just have to backtrack.
When you get to the village, go to Red Buffalo Woman's house. There are a lot of lodges in the village, but only two that you can actually enter. The big, tall, decorative one at the southern end of the village is the ranger station, and the small, squat, plain one a little north of that is Red Buffalo Woman's. Simply enter the lodge and she'll accept the package, giving you another one. Now you have to take this back to Gillian.
Go to the Sinsearach and ask to speak to the elders. (1)[edit]
So... you still have 5,000¥ hanging around, right? If so, go back to the street terminal and get Sharkey to drop you off at the Sinsearach. If not, you gotta walk all the way back. When you get there, ask to speak to the elders again. This time Gillian will ask you to find a fellow elf, Ilene Two Fists.
Go to Icarus Descending and ask Caleb about Ilene Two Fists.[edit]
You know the drill... if you have a grand left over, fly back out to the highway. If not, backtrack. Either way, get to the terminal so you can call a cab to the Renraku Arcology (or Downtown Seattle, if you're not fond of shortcuts) and walk to Icarus Descending. Once inside, talk to Caleb and tell him you're looking for information. Ask him about Ilene and he'll tell you that she's locked up in Hollywood Correctional.
Go to Hollywood Correctional and rescue Ilene. (2)[edit]
In case you forgot, Hollywood is in the left end of Redmond Barrens, surrounded by a concrete fence. Before you go, though, you need two things: a way to get inside, and a way to open the jail cell that holds Ilene.
The second one is easy. Her cell is Level 5 Maglocked, so you need either a Level 5 Maglock Passkey (20,000¥ from Alesandro Hobbs, whose contact you can purchase from Mortimer Reed for 1,500¥) or a high Electronics skill (6 or 7 is good). In this case, you can even use a Frag Grenade, since the prison has no alarm system to speak of and setting off the 'alarm' only affects in guards that happen to be on screen at the time.
The other thing, getting into the prison in the first place, may be slightly tougher, but still isn't much of a challenge. The game comes up with several creative ways to get you inside, but most are too expensive. If you'd rather throw money around than fire a gun, though, I guess I should at least let you know that including meeting costs, Sgt. Chillicutt can get you into Hollywood for the least amount of money (2,000¥ for the contact from Caleb and 3,000¥ for access). Henry J. Culver (6,500-7,250¥ total) and Sgt. Macklemann (14,500¥) aren't worth bothering with.
As I said, though, these ways are too expensive. As far as costs go, you can't beat free. All you have to be able to do is to kill -- at the most -- six moderately armed enemies. To do this, just walk right up to Hollywood (making sure you have decent weapons and equipment first) and go in. When the guard stops you, choose to open fire. If your stats are good enough to score a direct hit, you'll get inside, immediately attacked by two (weak) prison guards. If your shots "miss the mark," as the game says, you'll end up out front of the building, under attack by two security guards and a mage. If this happens, STAND IN ONE PLACE and fight them. After you polish them off, try again. Hopefully, all three bodies will still be on the screen. This way, if you miss again, you'll only be fighting one or two enemies because of the Genesis' limitations on rendering sprites. If you miss a third time, you won't be fighting any! Repeat this process until you finally get in. Take care of the aforementioned prison guards and make your way downward.
After going down through the two open doors, turn left and work your way up and to the left. That's where Ilene is -- the cell all the way in the upper-left corner. When you get there, open the cell door one way or another and talk to her. As I've mentioned elsewhere in this FAQ, you may need to target her with B in order to be able to talk to her.
Once you meet her, you'll exchange a few words before she makes her escape. She mentions that she'll be at the Jump House. As the game says, it looks like you'll have to risk the front door again. Not that it's a risk of any kind, since the guards here won't attack unless provoked. Oh well.
Go to the Sinsearach, speak to the elders, and join them. (2)[edit]
After you've backtracked to escape from Hollywood and are back out on the street, the only thing left to do is return to the Sinsearach. Make your way back (you shouldn't need me to tell you how by now) and ask to speak to the elders one last time. In another Dragon-Warrioresque question (see Step 8 in the "David Owlfeather" part of this walkthrough), Gillian will ask if you really want to join. Say "yes" and the ceremony will begin.
Afterward, Gillian will answer questions about Ellisia, the elf who Caleb or Ilene may have told you about, and Thon. She says that Vigore and Jarl are working for Thon... interesting. Finally, you'll ask about Frosty. In kind of a half-assed attempt to write dialogue that complements the plot mechanics, Gillian will refuse to tell you about Frosty until you have attained "wisdom," which is really just a way of saying you have to complete the Spirit Eyes quest (see the "David Owlfeather" entry in this subsection) before you can go on to beat the game. Bleh.
On the other hand, if you've already done that, Gillian will skip to Step 1 in Subsection c below. Either way, you've completed this part of the game, picking up a very good runner in Ilene along the way. Congratulations.