Kobold scout

[Sigreid]

I've got a new character that will be starting soon acting primarily as the party scout and I'm curious what people think. So, rogue scout x or rogue 1 shadow monk x with expertise in stealth and perception for maximum scouting goodness?

[DarkKnightJin]

For a one-shot, I ran a Shadow Monk 8/Rogue 2 once. He basically went full ninja.
His Stealth (w/ Expertise) was like +12, and he could cast Pass without Trace for 2 Ki points to get up to +22.
Basically, if he didn't want to be found while sneaking, he wasn't going to be found.

Doing something like that for a Kobold should work pretty well for you. My advice is to take 2/3 levels of Rogue at most, unless you absolutely MUST have the 6th level Expertise for some reason.

[Sigreid]

Thanks for the feedback and personal experience, it's really helpful.

[Great Dragon]

6th level Shadow Monk gives Shadow Step
11th Level Shadow Monk allows you to Vanish with Cloak of Shadows, without any apparent effort.
3rd level Rogue for your favorite Archetype.

The real choice is between Opportunist at 17th level Shadow Monk - which allows a Reaction (with 2d6 Sneak Attack) whenever someone hits your target - and Uncanny Dodge at 5th Level Rogue, and Expertise at 6th Level, and 5d6 Sneak Attack at 9th Level Rogue - if your doing this split anyway, you might as well go for the most punch.

So, it really depends on what you want, and how high the Game goes.
06th Level Game = 3 Rogue/3 Monk
09th Level Game = 3 Rogue/6 Monk
14th Level Game = 3 Rogue/11 Monk
20th Level Game = 9 Rogue/11 Monk

[XmonkTad]

Druid wildshape scouting is also a great way to scout starting at level 2. It also helps give pack tactics to lots of creatures that don't otherwise get it, as well as erase the terrible str score that kobolds get.
Otherwise I would stick with pure rogue. Again, pack tactics will help your SA land reliably and so scaling that as high as possible is a great way to scale damage. Although it does hurt to not get pass without a trace from monk, so your scouting ability goes down.

[Sigreid]

Good puts. I will say that my emphasis is on the scout portion over damage and I've basically played all full casters so far in 5e so I'm avoiding going that route. Even though I love druids.

[MilkmanDanimal]

If your goal is advance scout and thereby focusing on mobility, Scout is a good archetype for that, but with the focus it sounds like you have on being sneaky, three levels of Rogue and Arcane Trickster gets you a few useful cantrips plus access to a few first-level spells, plus an incredibly useful invisible Mage Hand. Pair that with your Shadow Monk levels, and you could do all sorts of fun things.