(Also, would you guys prefer general descriptions of where things are/distances in combat - theater of the mind, or would you prefer a grid map?)

I’d like to try descriptions and go a little more free flow,  in general, maybe save grids for a major fight if needed

Initiative 12

Pops uses Minor Illusion to make a 5ft square of dust rise up around Dawn, giving her advantage on her next attack for being unseen and providing disadvantage on the next attack against her. 

(Rolling initiative for the kobolds while we wait for Deekin: 12.  For the combat, I figure I'll just do one roll for the enemies, then any allies with a higher initiative can take their turns in whatever ordre they want, then enemies all take their turns, then players can all go, again in any order they want.  Keeps it a little more open and might save time so you don't necessarily have to wait for another player before you can take your turn to keep things moving.  Also allows you to shift what ordre you take your turns if desired for strategic reasons (let one player cast a spell or perform some action before another does something to capitalize on it)

And initiative for the humans: 7

Quote from VanderLegion >>

(Rolling initiative for the kobolds while we wait for Deekin: 19.  For the combat, I figure I'll just do one roll for the enemies, then any allies with a higher initiative can take their turns in whatever ordre they want, then enemies all take their turns, then players can all go, again in any order they want.  Keeps it a little more open and might save time so you don't necessarily have to wait for another player before you can take your turn to keep things moving.  Also allows you to shift what ordre you take your turns if desired for strategic reasons (let one player cast a spell or perform some action before another does something to capitalize on it)

And initiative for the humans: 1

Say it ends up:

Dawn
Kobolds
Pops
Rocksmasher
Deekin
Humans

Dawn would go first, then the kobolds would go, then everyone (including dawn again) takes their turns in whatever ordre, then kobalds, then players, etc.  Speeds up the combat a bit by making it so if the first person isn't around to take their turn (pops in this case) it doesn't hold up the entire party until they show up. T he other players are free to take their turns, then pops would get his turn when he came back, then immediately go to the monsters and the next round of combat.

(It looks like I forgot to introduce myself, so pretend this happened on the road)

Before you is a lithe ginger furred humanoid feline. The last 3 inches of his tail us snow white and he has a white patch on his throat. Two shoulder sheaths with daggers. A reaper at his side. He has a backpack with a bow on one side and a pair of nets on the other side.

"Hello my name is Chasing Dawn's Song you can call me Dawn."

After Deekin's response, I will shot another kolbold Attack: 8 Damage: 4 + 4

Unless his action effects me in some way

Deekin is not used to large buildings and open roads, and the current state of things has this little kobold quite flustered! Initiative: 19

Fumbling around in his pack you would think that Deekin is searching for a misplaced weapon, but you are rather surprised when he produces a lute instead of a blade. With his little clawed fingers Deekin starts playing an eerie tune while humming along in a raspy voice. Deekin looks at Rockcrusher and says, "A hammer with might can win the fight!" which gives the barbarian an unusual sense of inspiration.

[Deekin performs a song, and uses Bardic Inspiration on Rockcrusher]

? Perform: 15 ?

I don't know how performing works but I can do this, Bardic Inspiration:

"You can inspire others through stirring words or music. To do so, you use a bonus action on your turn to choose one creature other than yourself within 60 feet of you who can hear you. That creature gains one Bardic Inspiration die, a d6   - (Inspiring Rockcrusher, as a free action)

Once within the next 10 minutes, the creature can roll the die and add the number rolled to one ability check, attack roll, or saving throw it makes. The creature can wait until after it rolls the d20 before deciding to use the Bardic Inspiration die, but must decide before the DM says whether the roll succeeds or fails. Once the Bardic Inspiration die is rolled, it is lost. A creature can have only one Bardic Inspiration die at a time.

You can use this feature a number of times equal to your Charisma modifier (a minimum of once). You regain any expended uses when you finish a long rest."

(You still get your action as well. This is only a bonus action) 

I am also armed with a sling and the ability to use Pack Tactics: "You have advantage on an attack roll against a creature if at least one of your allies is within 5 feet of the creature and the ally isn’t incapacitated."  But for now I am just serenading you all with my fine Kobold music. I'm not able to find bardic songs on here, let alone how to use them. Is there something deeper that I need to look for or how does performance work?  (And I don't mind the sign language, although Deekin cannot understand it he thinks it is actually quite fascinated that a being can "talk" with their hands)

(Bards don’t work like that in 5e (just playing a song to give benefits). You have the bardic inspiration and you can take spells that give bonuses, but work as normal spells (use your action usually, use up spell slots if they aren’t cantrip a, etc). There’s not a “performance” to use in combat (though you might be able to find some use for it outside of combat perhaps))

Quote from Keneux >>

(You still get your action as well. This is only a bonus action) 

(Your character should have spells that you select when you create the character. Do you need help with that?) 

Quote from Keneux >>

(Your character should have spells that you select when you create the character. Do you need help with that?) 

Deekin bolsters Rocksmashers confidence, then tries to sling a rock into one of the kobolds.  Still flustered by the large buildings and the general situation, his aim is off and the bullet whizzes through the air directly at Rocksmasher, fortunately hitting the shield and bouncing off instead of striking the goliath.  Dawn had time to draw another arrow and let it fly into the kobolds.  His aim is true and he scores his second kill for the night.

Initiative rolls:
21 Dawn
19 Deekin
19 Kobolds
12 Pops
10 Rocksmasher
1 humans

Dawn took his action around for the first full round of combat.  I'll give Deekin the tiebreaker over the kobolds since he has a higher dex score, so Deekin gets another turn, then the kobolds will go,t hen all the players, and so on.  3 kobolds are down currently, 5 remaining.

Rocksmasher is right next to the kobolds, having charged in to strike one down.  The rest of you are probably about 20 feet away from them.  The woman is about 15 feet in front of them (to your right of the group), with the man and another 15 feet behind her.

Deekin whirls up another bullet in his sling and whips it toward the same target.   Attack: 7  Damage: 6

[His aim is slightly better this time]

This time Deekin's bullet bounces off of his targets temple, dropping the kobold instantly.

The kobolds finally get themselves together and rally to counterattack.  3 of them surround Rocksmasher, stabbing at him with their daggers, while the fourth one in the back moves around the goliath and attacks the woman.

Attacks at Rocksmasher:
Attack: 24 Damage: 6
Attack: 20 Damage: 4
Attack: 15 Damage: 5

Attack at the woman:
Attack: 17 Damage: 6

The first kobold sinks his dagger deep into the goliath's chest.  The second is not so lucky.  He slips on his friends blood right as he starts his swing, losing his balance and sinking his dagger into the third kobold's neck, dropping it before it's own swing at Rocksmasher can connect.  The final kobold reaches the woman and slashes her stomach, leaving her staggering.

(Back to the players)

Attack: 18 Damage: 5Rocksmasher glares at the kobald that stabbed him and swings his warhammer into his foe.