Help with a highwayman

[Afrodactyl]

Hi guys. I'm putting together a character who is going to be an ex-highwayman (he wasn't very good at it, so decided to do mercenary work instead). RP-wise, he still dips into his roguish habits when there's gold on the line, and thinks himself a bit of a charmer.

So far he's level six, having started as a fighter for three levels, into battle master, and then three levels into hunter ranger. I also went with pirate for the background (the locals recognise him from his criminal days).

I'm predominantly using dex weapons, namely a rapier, hand crossbow and a longbow.

What would be my best way to go from here? I was thinking rogue, for more criminal themed goodies, but I would get a skill boost/feat and an extra attack if I took fighter to 5.

[JackPhoenix]

Ex-highwayman sounds to me like "has a Criminal background (you can change the feature for the pirate feature, if that fits better)". Nothing more, nothing less. Why should you spend limited resources during leveling to represent something you left behind long ago?

[Afrodactyl]

Ex-highwayman sounds to me like "has a Criminal background (you can change the feature for the pirate feature, if that fits better)". Nothing more, nothing less. Why should you spend limited resources during leveling to represent something you left behind long ago?

I was thinking criminal, but went with pirate for the 'you can do very minor crimes and kind of get away with it', as I figured an inept highwayman might not have much in the way of criminal contacts.

As far as the levelling goes, I wanted to build the character with all the experiences he has from his previous lifestyle, whilst still maintaining usefulness in game . So tracking people through rough terrain to give them the whole 'stand and deliver' spiel, fighting dirty (battle master, Colossus Slayer, hunters mark, then sneak attack if I went with rogue), etc.

Is there a better option over rogue for the whole 'fighting dirty if I can't talk my way out of something' deal?

[Occasional Sage]

Absolutely agreed. Grow forward, not backward.

[Trum4n1208]

Looks good to me.

[SuchADiceGuy]

Which class you want to level up next depends on how you want your character to fight. When I think of a rogue, I think of a thief in an urban environment, or a cloaked assassin wielding a crossbow. The opponents that these guys face never see them at all. I picture a highwayman is more like a barbarian or fighter, who initially uses the advantage of surprise, but after the initial attack, they'll charge right out of the bush they were cowering behind and rush out to defeat their startled victims. So since you've already leveled up fighter, I'd recommend increasing that if you want to emphasize the skills your character learned in his past.

Could you explain what you mean when you say "fighting dirty," though? Because if you want to start sneak attacking people, running and hiding from foes, there's no better class than the rogue.