Hobgoblin Sky Pirate III - (Hobgoblin Bard of Valor)

This is another direction that I had decided I might go with this concept. In fact, as I desired to play a full caster, this one was ahead of the barbarian on the list of likelihoods. In the end I settled on the sorcerer option one I finally created the actual character. In the end, I had decided the fact that I had previously played a bard (granted only as far as level 4) settled me on sorcerer. Though that doesn't really make much sense given I have also recently played a sorcerer. Both bard and sorcerer are versatile enough classes that one might play very differently from another. That said, I also was feeling stubbornly determined to make best use of the Martial Training racial trait by taking a class that did not normally have martial weapons or armor proficiency. This is also what set me against Cleric and Druid while the firm desire to use a greatsword a la the picture settled me against Rogue.

For this I am a general 30 pt buy as allowed by the inspiring campaign, but I'm basically just copying the stats I gave the actual character.

1st Level Hobgoblin Bard

Str: 14

Dex: 12

Con: 15

Int: 14

Wis: 8

Cha: 15

HP: 10

AC: 13
Save DC: 12

Speed: 30 ft

Proficiency Bonus: +2

Darkvision 60ft
Martial Training: Greatsword, Rifle
Saving Face

Armor Proficiencies: Light Armor

Weapons: Simple Weapons, Hand Crossbows, Longsword, Rapier, Shortsword, Greatsword, Rifle

Tools: Drum, Horn, Organ

Saving Throws: Dexterity, Charisma
Languages: Common, Goblionid

Proficient Skills
Athletics (Pirate) +4
Deception (Bard) +4
Intimidation (Bard) +4
Perception (Pirate) +1
Performance (Bard) +4

Background: Pirate

Spellcasting
Bardic Inspiration (d6)

Cantrips: Friends, Vicious Mockery

Spell Slots: 2 (1st)

1st Level Spells: Bane, Longstrider, Silent Image, Thunderwave

Equipment
Leather Armor
Greatsword

Reasoning: This character is probably going to trend more towards the tricky style of magic with illusions and the like than the brutal side. Catching of the original character, I added in Longstrider to fill in for Jump in the terms of mobility assist. Thunderwave provides a boost of extra offense at need, though to start if she's using greatsword she won't be able to use it and her sword.

2nd to 5th Level

2nd Level - Jack of all Trades, Song of Rest (d6) +7 HP (17)
Spell: Healing Word

3rd Level - Bard College: Valor, Expertise: Deception, Intimidation, Combat Inspiration, Bonus Proficiencies, +7 HP (24)
Spell: Hold Person

4th Level - Ability Score Improvement: War Caster, +7 HP (31)
Cantrip: Minor Illusion
Spell: Invisibility

5th Level - Proficiency Bonus: +3, Bardic Inspiration (d8), Font of Inspiration, +7 HP (38)
Spell: Counterspell

Reasoning: I went for War Caster this early instead of increasing stats because the use of the Great Sword will be a lot harder to get around in this case than with a sorcerer which has the Subtle Spell metamagic. This means that early on she'd be struggling with low save DCs and low attack bonuses for her spells, but I think in the long run it's important to get this out early. Regarding spells, again, Counterspell just falls into the category of "too good to pass up". Healing Word was chosen because it's always good to have some healing on hand. I almost went with Cure Wounds as she is more front line, but decided to make it easier to heal at a distance. Also note that from this point she starts wearing breastplate.

5th Level Statistics

5th Level Hobgoblin Valor Bard

Str: 14

Dex: 12

Con: 15

Int: 14

Wis: 8

Cha: 15

HP: 38

AC: 15
Save DC: 13

Speed: 30 ft

Proficiency Bonus: +3

Darkvision 60ft
Martial Training: Greatsword, Rifle
Saving Face

Armor Proficiencies: Light Armor, Medium Armor, Shields

Weapons: Simple Weapons, Martial Weapons

Tools: Drum, Horn, Organ

Saving Throws: Dexterity, Charisma
Languages: Common, Goblionid

Proficient Skills
Acrobatics (Jack of all Trades) +2
Animal Handling (Jack of all Trades) +0
Arcana (Jack of all Trades) +3
Athletics (Pirate) +5
Deception (Bard, Expertise) +8
History (Jack of all Trades) +3
Insight (Jack of all Trades) +0
Intimidation (Bard, Expertise) +8
Investigation (Jack of all Trades) +3
Medicine (Jack of all Trades) +0
Nature (Jack of all Trades) +3
Perception (Pirate) +2
Performance (Bard) +5
Persuasion (Jack of all Trades) +3
Religion (Jack of all Trades) +3
Survival (Jack of all Trades) +0

Background: Pirate

Feat: War Caster

Spellcasting
Bardic Inspiration (d8)
Jack of all Trades
Song of Rest (d6)
College of Valor
Bonus Proficiencies
Combat Inspiration
Expertise: Deception, Intimidation
Font of Inspiration

Cantrips: Friends, Minor Illusion, Vicious Mockery

Spell Slots: 4 (1st) 3 (2nd) 2 (3rd)

1st Level Spells: Bane, Healing Word, Longstrider, Silent Image, Thunderwave
2nd Level Spells: Hold Person, Invisibility
3rd Level Spells: Counterspell

Equipment
Breastplate
Greatsword

6th to 10th Level

6th Level - Countercharm, Extra Attack, +7 HP (45)
Spell: Major Image

7th Level - +7 HP (52)
Spell: Freedom of Movement

8th Level - Ability Score Improvement: +1 Con and +1 Cha, +15 HP (67)
Spell: Dimension Door

9th Level - Proficiency Bonus +4, Song of Rest (d8), +8 HP (75)
Spell: Animate Objects

10th Level - Bardic Inspiration (d10), Expertise: Athletics, Perception, Magical Secrets, +8 HP (83)
Cantrip: Booming Blade
Magical Secrets Spell: Shield
Spell: Seeming

Reasoning: It might seem odd to not choose Performance for Expertise here, but given that performance is really a secondary aspect of this character, something she does between raids to keep morale up in the crew, it makes more sense that she'd opt for a place where she is a bit weaker than usual. As to spells, I decided on Shield because of the fact this character is a melee caster and my past experiences as a draconic sorcerer has shown me that Shield is amazing for such characters. Another odd choice for my magical secrets was in choosing a cantrip and taking booming blade. Granted that with Extra Attack I could be making two greatsword attacks but with Booming Blade I get some extra control and can be adding up to 3d8 to one attack even if they don't move, more than making up for the lost strike.
 

10th Level Statistics

10th Level Hobgoblin Valor Bard

Str: 14

Dex: 12

Con: 16

Int: 14

Wis: 8

Cha: 16

HP: 83

AC: 15
Save DC: 15

Speed: 30 ft

Proficiency Bonus: +4

Darkvision 60ft
Martial Training: Greatsword, Rifle
Saving Face

Armor Proficiencies: Light Armor, Medium Armor, Shields

Weapons: Simple Weapons, Martial Weapons

Tools: Drum, Horn, Organ

Saving Throws: Dexterity, Charisma
Languages: Common, Goblionid

Proficient Skills
Acrobatics (Jack of all Trades) +3
Animal Handling (Jack of all Trades) +1
Arcana (Jack of all Trades) +4
Athletics (Pirate, Expertise) +10
Deception (Bard, Expertise) +11
History (Jack of all Trades) +4
Insight (Jack of all Trades) +1
Intimidation (Bard, Expertise) +11
Investigation (Jack of all Trades) +4
Medicine (Jack of all Trades) +1
Nature (Jack of all Trades) +4
Perception (Pirate, Expertise) +7
Performance (Bard) +7
Persuasion (Jack of all Trades) +5
Religion (Jack of all Trades) +4
Survival (Jack of all Trades) +1

Background: Pirate

Feat: War Caster

Spellcasting
Bardic Inspiration (d10)
Jack of all Trades
Song of Rest (d8)
College of Valor
Bonus Proficiencies
Combat Inspiration
Expertise: Deception, Intimidation
Font of Inspiration
Counter Charm
Extra Attack
Magical Secrets

Cantrips: Booming Blade, Friends, Minor Illusion, Vicious Mockery

Spell Slots: 4 (1st) 3 (2nd) 3 (3rd) 3 (4th) 2 (5th)

1st Level Spells: Bane, Healing Word, Longstrider, Shield, Silent Image, Thunderwave
2nd Level Spells: Hold Person, Invisibility
3rd Level Spells: Counterspell, Major Image
4th Level: Freedom of Movement, Dimension Door
5th Level: Seeming

Equipment
Breastplate
Greatsword

11th to 15th Level

11th Level - +8 HP (91)
Spell: Programmed Illusion

12th Level - Ability Score Improvement: +2 Cha, +8 HP (99)

13th Level - Proficiency Bonus +5, Song of Rest (d10), +8 HP (107)
Spell: Mirage Arcane

14th Level - Magical Secrets, Battle Magic, +8 HP (115)
Magical Secrets: Simulacrum, Spirit Guardians

15th Level - Bardic Inspiration (d12), +8 HP (123)
Spell: Mind Blank

Reasoning: Spiritual Guardians may seem a bit low level to be taking with Magical Secrets, but I've found that the highest level spells are increasingly situational in use while the lower level spells have more broad applicability. In this case, she can create a small host of spirits to fight beside her. Aside from that she did choose the ability to create a semi-independent copy of herself.

15th Level Statistics

15th Level Hobgoblin Valor Bard

Str: 14

Dex: 12

Con: 16

Int: 14

Wis: 8

Cha: 18

HP: 123

AC: 15
Save DC: 17

Speed: 30 ft

Proficiency Bonus: +5

Darkvision 60ft
Martial Training: Greatsword, Rifle
Saving Face

Armor Proficiencies: Light Armor, Medium Armor, Shields

Weapons: Simple Weapons, Martial Weapons

Tools: Drum, Horn, Organ

Saving Throws: Dexterity, Charisma
Languages: Common, Goblionid

Proficient Skills
Acrobatics (Jack of all Trades) +3
Animal Handling (Jack of all Trades) +1
Arcana (Jack of all Trades) +4
Athletics (Pirate, Expertise) +12
Deception (Bard, Expertise) +14
History (Jack of all Trades) +4
Insight (Jack of all Trades) +1
Intimidation (Bard, Expertise) +14
Investigation (Jack of all Trades) +4
Medicine (Jack of all Trades) +1
Nature (Jack of all Trades) +4
Perception (Pirate, Expertise) +9
Performance (Bard) +9
Persuasion (Jack of all Trades) +6
Religion (Jack of all Trades) +4
Survival (Jack of all Trades) +1

Background: Pirate

Feat: War Caster

Spellcasting
Bardic Inspiration (d12)
Jack of all Trades
Song of Rest (d10)
College of Valor
Bonus Proficiencies
Combat Inspiration
Expertise: Deception, Intimidation
Font of Inspiration
Counter Charm
Extra Attack
Magical Secrets
Battle Magic

Cantrips: Booming Blade, Friends, Minor Illusion, Vicious Mockery

Spell Slots: 4 (1st) 3 (2nd) 3 (3rd) 3 (4th) 2 (5th) 1 (6th) 1 (7th) 1 (8th)

1st Level Spells: Bane, Healing Word, Longstrider, Shield, Silent Image, Thunderwave
2nd Level Spells: Hold Person, Invisibility
3rd Level Spells: Counterspell, Major Image, Spirit Guardians
4th Level: Freedom of Movement, Dimension Door
5th Level: Seeming
6th Level: Programmed Illusion
7th Level: Mirage Arcane, Simulacrum
8th Level: Mind Blank

Equipment
Breastplate
Greatsword

16th to 20th Level

16th Level - Ability Score Improvement +2 Str, +8 HP (131)

17th Level - Proficiency Bonus +6, Song of Rest (d12) +8 HP (139)
Spell: Foresight

18th Level - Magical Secrets, +8 HP (147)
Magical Secrets: Weird, Wish

19th Level - Ability Score Improvement: +2 Cha, +8 HP (155)

20th Level - Superior Inspiration, +8 HP (163)

Reasoning: Wish is a really hard spell to pass up. In addition, the fact that bards can have three separate ninth level spells is amazing. In this case I went for a bit more in the way of the illusions and such for the most part, with Foresight being a bit more protection in a fight. Wish sort of represents the idea of illusions so convincing that they become real.

20th Level Statistics

15th Level Hobgoblin Valor Bard

Str: 16

Dex: 12

Con: 16

Int: 14

Wis: 8

Cha: 20

HP: 163

AC: 15
Save DC: 19

Speed: 30 ft

Proficiency Bonus: +6

Darkvision 60ft
Martial Training: Greatsword, Rifle
Saving Face

Armor Proficiencies: Light Armor, Medium Armor, Shields

Weapons: Simple Weapons, Martial Weapons

Tools: Drum, Horn, Organ

Saving Throws: Dexterity, Charisma
Languages: Common, Goblionid

Proficient Skills
Acrobatics (Jack of all Trades) +4
Animal Handling (Jack of all Trades) +2
Arcana (Jack of all Trades) +5
Athletics (Pirate, Expertise) +15
Deception (Bard, Expertise) +17
History (Jack of all Trades) +5
Insight (Jack of all Trades) +2
Intimidation (Bard, Expertise) +17
Investigation (Jack of all Trades) +5
Medicine (Jack of all Trades) +2
Nature (Jack of all Trades) +5
Perception (Pirate, Expertise) +11
Performance (Bard) +11
Persuasion (Jack of all Trades) +8
Religion (Jack of all Trades) +5
Survival (Jack of all Trades) +2

Background: Pirate

Feat: War Caster

Spellcasting
Bardic Inspiration (d12)
Jack of all Trades
Song of Rest (d12)
College of Valor
Bonus Proficiencies
Combat Inspiration
Expertise: Deception, Intimidation
Font of Inspiration
Counter Charm
Extra Attack
Magical Secrets
Battle Magic
Superior Inspiration

Cantrips: Booming Blade, Friends, Minor Illusion, Vicious Mockery

Spell Slots: 4 (1st) 3 (2nd) 3 (3rd) 3 (4th) 2 (5th) 2 (6th) 1 (7th) 1 (8th) 1 (9th)

1st Level Spells: Bane, Healing Word, Longstrider, Shield, Silent Image, Thunderwave
2nd Level Spells: Hold Person, Invisibility
3rd Level Spells: Counterspell, Major Image, Spirit Guardians
4th Level: Freedom of Movement, Dimension Door
5th Level: Seeming
6th Level: Programmed Illusion
7th Level: Mirage Arcane, Simulacrum
8th Level: Mind Blank
9th Level: Foresight, Weird, Wish

Equipment
Breastplate
Greatsword

Some 5e Builds