Best gear progression for Wanderer class

As of Patch 1.05 it is possible to buy the Master Key from Domhnall of Zena for 5000 souls, after you beat Blightown.

There are two items I would suggest:

• Master Key: This will allow you to get into multiple places earlier. It is possible to buy this in-game, but not until much later into the game (by which point you may not find a use for it anymore).
• Black Firebomb: This will allow you to easily kill the Asylum Demon the first time you see him in the Undead Asylum. Doing so will grant you the Great Demon Hammer.

The consumable items have no importance, and are a complete waste of a starting gift in my opinion, except for the fire bombs.

In response to your second question, starting as thief and choosing the master key would result in you having two master keys.

There are three classes I would suggest for a new player:

• Cleric: The cleric starts with good stats all around, so you shouldn't have too much trouble dealing with early enemies. However, the most important thing about the cleric is that it starts with the healing miracle. This will grant you five extra heals at the start of the game, which is immensely helpful (especially for a new player), since it gives you more room for error. The largest problem with the cleric is that its starting armor and dexterity are not that great (although if you plan to go with a strength or faith build, the low dexterity doesn't matter). However, it shouldn't take you long to replace your armor, and it will only take a few levels to boost your dexterity.

• Sorcerer: The sorcerer starts with the Soul Arrow spell, which deals high damage early on, allowing you to safely kill enemies from a distance (including some of the early bosses). You will only start with 30 casts of Soul arrow, which really isn't a lot, but you can buy another copy of Soul Arrow from Rickert of Vinheim as soon as you exit the Undead Asylum. The second copy will allow you to cast Soul Arrow 60 times, which enough to ensure you'll never run out. The biggest problems a Sorcerer faces is that they are very fragile (you'll usually die in 1-2 hits), and there non-magic damage is very low (although there are only a handful of magic resistant enemies in the game).

• Warrior: The warrior starts with well-rounded stats, and good equipment. You shouldn't run into too many problems early in the game. Since his starting strength and dexterity are equally, you have the choice of going with either a dexterity or strength build. I would suggest dexterity myself, since a bow makes the game a lot easier.

Strength or Dexterity?

The last thing I want to touch on is deciding between making a Dexterity or Strength character. If you decide to make an int or faith based character, you can safely ignore this section.

The key difference between Strength and Dexterity is the type of weapons you use. Strength favours weapons like Axes, long swords, and great swords; where as Dexterity favours spears, katanas, and curved swords. In general, there aren't any huge differences between the two as far as damage output goes, and is just a matter of personal preference.

However, there is one thing to consider: bows. Although all bows scale with strength, it is very low, whereas all bows have very high scaling with dexterity. Due to this you can easily dispatch enemies from a distance with your bow. I cannot emphasis how helpful this will be throughout the game. Not only does it let you dispatch enemies before they get to you, but also allows you to dispose of archers as soon as you see them, instead of being forced to dodge their arrows as you fight your way to them. Due to this, I highly recommended a dexterity build over a strength build.