Quickleaf
Legend
[MENTION=54846]Rechan[/MENTION]
By my ancestor's beards, love the mastiff! Woof
[MENTION=6682807]Emka[/MENTION]
First about the party composition: Let him/her play a cleric, you'll be fine. Just encourage them to take some evasion oriented class features/feats/powers, follow Rechan's advice, and if you have it check out the "Party Building" article in Dragon#394.
About the pathfinding skill challenge: Be careful here, these sorts of things can be incredibly tedious for players. Here's my thinking...
1. You need a compelling reason to run overland travel/find the path as a skill challenge. If you can't think of anything beyond "get to the destination" either handwave it or reduce it to a group skill check (where if half the PCs succeed the group succeeds...perhaps allowing multiple checks). Examples of this would be a time limit to reach the destination or needing to keep a low profile while traveling.
2. A real feeling of travel and exploration that offers a development of the story/setting. Think of this as rich descriptions coupled with mini-hazards and challenges along the way. For example, traveling through the woods the PCs might stumble upon a faerie trod and it's mischievous thieving sprites, or pitch their tents at an old ranger's camp where they find an encoded military map.
3. Lastly, as you point out, what are the consequences of failure? And, as with the loss of surges, you've also identified that it's not about whether you reach the destination but under what conditions. Generally docking surges is boring and can feel arbitrarily punitive to players (others may disagree with me here). Loss of surges is fine when piggybacked on another more interesting consequence. For example, a fight against someone you really didn't want to fight (cause they're good-aligned or extremely powerful), or an NPC suffers, or the PCs learn misinformation/are deceived, etc.
There's a lot more to running skill challenges and criticisms/fixes to the RAW skill challenge rules out there, but the above should get you by to start.
By my ancestor's beards, love the mastiff! Woof

[MENTION=6682807]Emka[/MENTION]
First about the party composition: Let him/her play a cleric, you'll be fine. Just encourage them to take some evasion oriented class features/feats/powers, follow Rechan's advice, and if you have it check out the "Party Building" article in Dragon#394.
About the pathfinding skill challenge: Be careful here, these sorts of things can be incredibly tedious for players. Here's my thinking...
1. You need a compelling reason to run overland travel/find the path as a skill challenge. If you can't think of anything beyond "get to the destination" either handwave it or reduce it to a group skill check (where if half the PCs succeed the group succeeds...perhaps allowing multiple checks). Examples of this would be a time limit to reach the destination or needing to keep a low profile while traveling.
2. A real feeling of travel and exploration that offers a development of the story/setting. Think of this as rich descriptions coupled with mini-hazards and challenges along the way. For example, traveling through the woods the PCs might stumble upon a faerie trod and it's mischievous thieving sprites, or pitch their tents at an old ranger's camp where they find an encoded military map.
3. Lastly, as you point out, what are the consequences of failure? And, as with the loss of surges, you've also identified that it's not about whether you reach the destination but under what conditions. Generally docking surges is boring and can feel arbitrarily punitive to players (others may disagree with me here). Loss of surges is fine when piggybacked on another more interesting consequence. For example, a fight against someone you really didn't want to fight (cause they're good-aligned or extremely powerful), or an NPC suffers, or the PCs learn misinformation/are deceived, etc.
There's a lot more to running skill challenges and criticisms/fixes to the RAW skill challenge rules out there, but the above should get you by to start.