Where to go with this rogue

[Camman1984]

I am about to reach my first 'decision point' with my little rogue, her stats are below

race
half sun-elf with booming blade cantrip

str 10
dex 16
con 12
int 8
wis 14
cha 16
AC 16 (17 with shield)
30 speed

custom pirate background
level 1 fighter
mariner fighting style for mobility

level 3 rogue
swashbuckler archetype

currently armed with
scimitar, buckler, light crossbow, chain shirt

she currently fights as a skirmishers and I really enjoy it, moving in (climbing and swimming if needed) booming blade with some sneak attack (every turn with swashbuckler ability) then running away.

next level is my first ASI level

I know mechanically the +2 dex is my best bet as it improves everything I need, but to me it's boring.

my other choices are

crossbow expert for sword xbow double, but will lose the shield and booming blade use.

my favourite option is to go as a wizard Hunter and take mage slayer, use my high speed to run in and booming sneak attack, hopefully making them loose a concentration spell. then the caster has to decide, move away and get booming blade + sneak attack AAO, cast and get the sneak attack AAO or disengage and lose a spell.

any suggestions? am I missing a really fun trick? she is meant to be an expirate, which i why I wanted a mobile blade, but she is beginning to learn that wizards are her worst foe and wants to deal with them.

[Camman1984]

oh, I am running out of the abyss (no spoilers please) with

a halfling warrior
a dragonborn barbarian
a human trickster cleric
a human wizard (not sure what school)

[djreynolds]

Go dex, then grab mage slayer at 8th or 10th level rogue.

[Camman1984]

that seems like the less interesting option.

would it be possible to get an item to boost my dexterity up to the 20 max instead of using stat boosts

[Citan]

oh, I am running out of the abyss (no spoilers please) with

a halfling warrior
a dragonborn barbarian
a human trickster cleric
a human wizard (not sure what school)
IF your Cleric pals tend to usually use Bless on allies, you included, pick up Mage Slayer: more flavorful, and potentially much better than just a plain DEX bump.

Otherwise... Well, it's always a personal choice, but I personally miss by just 1 often enough to feel bad about not taking DEX if I were in your place...^^

[Tauguy628]

Sentinal (don't take this if the barbarain or halfling takes this) greatly imporve your OAs. It also allows you to get sneak attack damage off turn more often, which is fun to say the least. However, this may make monsters target you more as it is a tanking feat, but this can be less of a problem once you hit rouge 5 and unlock uncanny dodge. Even as you are now, you mobilty should get you out of most sticky situations. If you work with the barbarian, this can also alow them to use reckless attack with less retribution which is good. Honestly, Just go with what you want. In general, 5e is not a game that requires optimization, so have fun with your rouge!

[djreynolds]

that seems like the less interesting option.

would it be possible to get an item to boost my dexterity up to the 20 max instead of using stat boosts

Possibly, maybe. What if you do not have any magic items, or it is a magic dagger vs something of dex.

If you use a shield often, shield master and expertise in athletics is my old standby. Its nice to attack with advantage

But dex will increase chances to hit, damage, and AC and skills

But have fun.

[ShirAhn]

I am about to reach my first 'decision point' with my little rogue, her stats are below

race
half sun-elf with booming blade cantrip

str 10
dex 16
con 12
int 8
wis 14
cha 16
AC 16 (17 with shield)
30 speed

custom pirate background
level 1 fighter
mariner fighting style for mobility

level 3 rogue
swashbuckler archetype

currently armed with
scimitar, buckler, light crossbow, chain shirt

she currently fights as a skirmishers and I really enjoy it, moving in (climbing and swimming if needed) booming blade with some sneak attack (every turn with swashbuckler ability) then running away.

next level is my first ASI level

I know mechanically the +2 dex is my best bet as it improves everything I need, but to me it's boring.

my other choices are

crossbow expert for sword xbow double, but will lose the shield and booming blade use.

my favourite option is to go as a wizard Hunter and take mage slayer, use my high speed to run in and booming sneak attack, hopefully making them loose a concentration spell. then the caster has to decide, move away and get booming blade + sneak attack AAO, cast and get the sneak attack AAO or disengage and lose a spell.

any suggestions? am I missing a really fun trick? she is meant to be an expirate, which i why I wanted a mobile blade, but she is beginning to learn that wizards are her worst foe and wants to deal with them.

Well, if you want something not boring have you considered "Defensive Duelist" (FEAT)?

Once you get fighter 3 and Riposte you have allot of options for your reaction.
Options:
1. they attack you and miss, (battlemaster Riposte) You can use your reaction to make an attack (with sneak attack)
2. they attack you and just barely hit (defensive duelist) Add your proficiency bonus to AC. And you are not hit (oohyeah! This is not boring)
3. they attack you and you know you cant get away this time, (uncanny dodge like a boss)

[Biggstick]

It might be the boring option, but +2 Dex is going to serve you better in the long run. Dexterity does so many good things for you (AC, initiative, Dex saves, Dex checks, attack rolls, damage done), that I honestly couldn't imagine a better choice.

[djreynolds]

It might be the boring option, but +2 Dex is going to serve you better in the long run. Dexterity does so many good things for you (AC, initiative, Dex saves, Dex checks, attack rolls, damage done), that I honestly couldn't imagine a better choice.

I agree with dex too, but sentinel could work if he teams up with the barbarian

[JellyPooga]

If you have Expertise in Athletics, then Shield Master may be an option; early "Evasion" (until you get the real thing), bonus vs. Single target spells and bonus action Shove is great stuff and you're using a shield anyway.

Sentinel is amazing, as others have said, but you'll really want to work on getting your AC higher before taking it, otherwise you'll just find yourself dying quicker. If no-one else has it by then, taking Sentinel at 8th or 10th might be better.

Having said that and assuming you are encountering a lot of spellslingers...go with your gut and take Mage Slayer. Is it the "optimal" choice? Probably not, but who cares? Mage Slayer will make you feel like a wizard-hunter, force those decisions that you talk about and you'll feel faithful to your character, doing what you envision them to be. If you want to go whole hog down that path, take Lucky at 8th level as "magic resistance", grab Expertise in Arcana at 6th to out-smart them, see if you can find any magic items that improve your saves against spells or are particularly potent vs. Wizards; a Wand of Silence, perhaps.

Taking the Dex bump is valuable, but essentially it's also kinda boring; nothing changes as far as play style or actions; you just hit and are missed a bit more often. 16 Dex is perfectly adequate up to 12th level (by which point you'll probably want to bump it up, but even then it's by no means a necessity).

[Deadandamnation]

Imho mobility:

It gives you the ability to abuse cunning Action:

Dive in, stab, disengage for free than move away doubling your Speed or Stealthing yourself.

[Camman1984]

my swashbuckling already gives me a limited version of free disengage.

I really like the idea of the shield master, bashing people around, unsure how I get advantage from it though as I attack, then shove them for free 5ft, the only issue is my mediocre strength, so my athletics will always be weaker than a 'proper' fighter.

sentinel doesn't really appeal to me, it doesn't feel right for the character, unless she pulls out her whip and I re-skin sentinel as a 'tripping' attack (which unfortunately doesn't knock them prone).

I think when all is said and done I will end up going mage Hunter as we aren't an optimised group and it might be fun as spell casters seem to be ourounded biggest threat at the moment

[Deadandamnation]

With Expertize into Athletic you are good at Bashing as a str fighter even with +0.

Your bonus Will range from 6 to 8 in mid levels while theirs range from 8 to 9 (assuming a 20 Str score), you can fill the gap with a Magic items that boost Str if you are really concerned.

But I think that the anti-mage route it's Pretty good.

If that was me I think that Ranger (Hunter or Hound)/ Rogue (Assassin or thief) would be my choice.
Not a skirmisher anymore but more like a presence they have to fear.

No shield at all, Just some sort of poisoned daggers, apply some kind of poison Is your #1 goal, a poisoned wizard can't cast at all your #2 goal is to break concentration and a massive damage with a single strike help a lot.

What i dislike of Mage Killer is that if you face a tanky mage (like a Cleric) they Will target you with some sort of wis-based spell and you are toast even if you can SA again so i like an approach that's a lot more sneaky ;)

Resilient: Wisdom is another feat to consider, probably @lvl 8 imho

[Camman1984]

I am hoping the advantage to saves against spells at close range provided by the mage slayer should hopefully help to reduce that risk, and hopefully if it is a high value target like a cleric, the barbarian in the party will also be keeping a good chunk of his attention :)

will need to find ways to improve my saves, have proficiency in str and constitution, my dex and cha are both pretty high but not prof so all of my saves are currently pretty middle of the road.