So I've been experimenting with a build for a skillmonkey character that I came up with several months ago and that I've been revisiting (I have no idea if I'll ever play this character; so far it's just an interesting thought experiment). I originally planned it as an eladrin rogue multiclassing into bard through the Bardic Ritualist MC feat (I'd be choosing to train in Arcana through that feat); that gets me eight trained skills right off the bat. I'd also take jack-of-all-trades as my paragon path and sage of ages as my epic destiny (the MC feat will allow me to take that as my epic destiny); the combination of both will cause major boosts to some of my skills. I'll also be taking various feats along the way to boost my other skills. I liked the original build I had planned, but there are two things I came across that are forcing me to rethink my build.

One: I could accomplish a similar thing and get similar skill boosts by using human as my character's race instead of eladrin (the bonus skill I'd be choosing is in the rogue's skill list, so this works). The character's DEX might not be as good, and overall stat layout might not be the greatest compared to using eladrin as the race, but I'm not looking for the most optimal quality build, and I'm pretty sure human will still get the job done.

Two: this build is currently using pre-Essentials rogue. I keep forgetting about the Essentials classes, and I remembered the Essentials thief. One feature, and a low-level feature of the Thief at that, is Skill Mastery at level 2. That would allow Dungeoneering to be trained at a lower level, freeing up another skill to be trained with the Advanced Dabbler paragon path feature at level 16 (I'll probably train History with that since my build currently has me taking History Skill Training to allow other bonuses to stack up). Not to mention that other features of the thief would help out in combat to make up for what attack powers would be lost by going Essentials thief instead of pre-Essentials rogue.

Since it might help give a better idea of what I had planned with this pre-Essentials rogue build and whether or not I should switch to thief (or if I shouldn't and I'm just missing something obvious with my feats or power selection), I'll share what I have for those. Keep in mind with the feats that I haven't gotten a specific order set in stone, even though they are sectioned off into heroic-tier, paragon-tier, and epic-tier.

For the Eladrin variant:

Powers
Spoiler
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Level 1 - Deft Strike, Sly Flourish, Fey Step (racial), Dazing Strike, Easy Target
Level 2 - Fast Hands (Thievery Utility)
Level 3 - Trickster's Blade
Level 5 - Mocking Strike
Level 6 - Insightful Warning (Arcana Utility)
Level 7 - Rogue's Luck
Level 9 - Vexing Sting
Level 10 - Daring Gamble
Level 13 - replace Dazing Strike with Tornado Strike
Level 15 - replace Easy Target with Vicious Slash
Level 16 - Insightful Riposte (Insight Utility)
Level 17 - replace Trickster's Blade with Hounding Strike
Level 19 - replace Mocking Strike with Feinting Flurry
Level 22 - Dazzling Acrobatics
Level 23 - replace Rogue's Luck with Blindside
Level 25 - replace Vexing Sting with Rogue's Resurgence
Level 27 - replace Tornado Strike with Perfect Strike
Level 29 - replace Vicious Slash with Immobilizing Strike


Feats
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Heroic-tier
Bardic Ritualist (Ritual Caster)
Bard of All Trades
Backstabber
Versatile Duelist
Two-Fisted Shooter
Crossbow Expertise

Paragon-tier
Heavy Blade Expertise
Distant Advantage
Bardic Knowledge
Skill Training - History
Fey Gambit
Feywild Protection

Epic-tier
Shadow Eyes
Blind-Fight
Flanking Maneuver
Unfettered Stride
Superior Initiative
Artful Provocation


For the Human variant:

Feats
Spoiler
Show
Heroic-tier
Bard of All Trades
Distant Advantage
Backstabber
Two-Fisted Shooter
Crossbow Expertise

Paragon-tier
Heavy Blade Expertise
Deadly Draw
Skill Training - History
Bardic Knowledge
Agile Opportunist
Bloody Tenacity

Epic-tier
Shadow Eyes
Blind-Fight
Flanking Maneuver
Unfettered Stride
Superior Initiative
Artful Provocation

Class/skill powers are the same.