Hand Crossbow of Warning. This magic weapon warns Bob of danger. While the weapon is on his person, he has advantage on initiative rolls. In addition, he can’t be surprised, except when incapicated by something other than nonmagical sleep. The weapon magically awakens him if he is sleeping naturally when combat begins.

War mage. A 1-inch diameter ruby (Ruby of the War Mage) sits at the bottom of Bob's Hand Crossbow, allowing him to use it as a spellcasting focus, and cannot be removed for as long as he is attuned to the ruby. In addition, through training and discipline, Bob is able to perform somatic components even while his hand is occupied by the crossbow.

Component Pouch.  Bob also carries a component pouch at his side in the event he is without his crossbow.

Multiattack. Bob makes two dagger or pistol attacks and uses Efficient Mockery

Dagger of Venom. Melee Weapon Attack: +7 to hit, reach 5 ft., one target. Hit: 6 (1d4 + 4) piercing damage.

Hand Crossbow. Ranged Weapon Attack: +4 to hit, range 30/120 ft., one target. Hit: 7 (1d6 + 4) piercing damage.

Efficient Vicious Mockery. The bard targets one creature within 30 feet of it. If the target can hear the bard, the target must succeed on a DC 15 Charisma saving throw or have disadvantage on ability checks, attack rolls, and saving throws until the start of the bard’s next turn, and take 3d10 psychic damage [roll]3d10[/roll].  On a succesful save, the target takes half as much damage. 

Spellcasting. Bob is a 5th level spellcaster who knows the following spells, using Charisma as the spellcasting ability (spell save DC 15):

At will: light, mage hand, prestidigitation

4 1st level slots: charm person, dissonant whispers, faerie fire, detect magic, dominate person, tasha's hideous laughter

3 2nd level slots: invisibility, enlarge/reduce, suggestion, silence, hold person, slow

3 3rd level slots: haste, counterspell, zone of truth

3 4th level slots: confusion, dimension door

1 5th level spell slot: synaptic static, mislead

Constructive Criticism (recharge on 3-6). Bob targets one creature within 30 feet of him that can hear and understand him.  That creature can now add a d10 to one ability check, attack roll, or saving throw it makes.  Once rolled the effect on that creature ends, whether the criticism is effective or not. 

Cutting words (recharge on a 4-6).  When a creature Bob can see within 60 feet of him makes an attack roll, ability check, or damage roll, he can use his reaction to roll a d10 and subtract that from the creature's roll.  In addition, the creature must be able to hear and understand Bob for this to take effect.

At arm's length.  When a creature moves within 5 feet of Bob, he can use his reaction to move up to half his movement speed.  This movement doesn't provoke opportunity attacks.