Advice on Rogue/Ranger multiclass

[OverDemon]

So I'm currently level 3 with a Wood Elf Rogue in Adventure League. I decided that I wanted to play my first ranged damage dealer, but didn't like how the Ranger worked and wanted some more skills/stealth than the Fighter allowed, so I went Rogue and so far I've had fun :smallsmile:

However, I'm approaching the point-of-no-return at level 5 (which is the level I can no longer completely alter my character in AL) and while I had a plan, I've recently become uncertain about that plan which is why I'm seeking a bit of advice.

So, the plan was to go 1-5 in Rogue, taking the Scout subclass, and then go 1-5 in Ranger (level 6-10), taking the Gloomstalker subclass, and then take the rest of levels in Rogue if I ever got that far.

The idea was to sacrifice an ASI, and high-level Sneak Attack and high-level Rogue and archetype abilities for the Archery fighting style, Extra Attack, a few spells AND the invisibility in darkness and initiative boost and extra first-round attack from Gloomstalker. The result, as I see it, would be a character with nearly all the good stuff from Rogue, BUT also more well-rounded with extra damage, attack, and spells. It would have a MASSIVE initiative boost, be able to kick ass on the first round, but also remain relevant in extended combat and without Sneak Attack thanks to its extra damage and attacks.

However, recently I've gotten a little uncertain and considered whether I should stick to only 3 levels in Ranger, just to get the Gloomstalker level 3 abilities and Scout level 17 ability OR just drop multiclassing completely and make a level 20 Scout Rogue.

Part of this reason is that I can't help but wonder whether losing out on the Scout's Sudden Strike is a really bad thing? I've been a bit sceptical about using my bonus action on another attack with Sneak Attack since I've often want to use that on Cunning Action (Hide), and I've also thought about whether Extra Attack, fighting style and spell make up for it Sudden Strike? But 2 Sneak Attack is a LOT of damage.
The other reason is that I'm wondering if delaying Rogue abilities will make me feel weak for a long time.

So, I hope that getting some advice from others might help me feel more confident about my plan, or point out why another path might make more sense.

Thank you in advance.

[CTurbo]

I think adding 5 levels of Gloom Stalker is a huge boost for an archer Rogue. I'd go for it. Rogue 5/Ranger 5 is not going to feel any weaker than Rogue 10. The only time you're going to feel behind is Rogue 5, Ranger 1 since 1 level of Ranger doesn't get you much at all.

I wouldn't stress about losing a 17th level ability as you're not likely to get there ever and even if you do, it would take a really really long time to get there. Scout 15/GS 5 is very very strong. As an archer, I think having the second attack is EXTREMELY important effectively doubly your chance for sneak attack. Take Sharpshooter and only use the -5/+10 with your second attack only when you hit with your first attack and used your sneak damage. The +10 from SS roughly equals 3d6 sneak damage on average.

[Bobthewizard]

I don't know the right answer if you are planning on playing a level 20 character. I never get that far so I like to plan builds that work from level 1-10+.

For those levels, I think rogue/gloomstalker works great. I would start gloomstalker 5 for extra attack and then the rest rogue. You get a fighting style, extra attack, a 3rd attack in the first round and hunter's mark. With the extra attacks, hunter's mark will make up for the lost 2-3 sneak attack dice.

[OverDemon]

I think adding 5 levels of Gloom Stalker is a huge boost for an archer Rogue. I'd go for it. Rogue 5/Ranger 5 is not going to feel any weaker than Rogue 10. The only time you're going to feel behind is Rogue 5, Ranger 1 since 1 level of Ranger doesn't get you much at all.

I wouldn't stress about losing a 17th level ability as you're not likely to get there ever and even if you do, it would take a really really long time to get there. Scout 15/GS 5 is very very strong. As an archer, I think having the second attack is EXTREMELY important effectively doubly your chance for sneak attack. Take Sharpshooter and only use the -5/+10 with your second attack only when you hit with your first attack and used your sneak damage. The +10 from SS roughly equals 3d6 sneak damage on average.

That's nice to hear, thanks. And yeah, I have a tendency to "over-plan" these things ^^

About feats, you mention Sharpshooter and it's definitely a feat I've planned to take eventually. However, I've thought about taking Elven Archery as my first feat. The +1 to Dex would give me 18 Dex and the reroll when I have Advantage seemed interesting.

Is there a need to rush 20 Dex or is 18 fine? That way I could take Sharpshooter as my second ASI, the level before I get Extra Attack.

[Gignere]

That's nice to hear, thanks. And yeah, I have a tendency to "over-plan" these things ^^

About feats, you mention Sharpshooter and it's definitely a feat I've planned to take eventually. However, I've thought about taking Elven Archery as my first feat. The +1 to Dex would give me 18 Dex and the reroll when I have Advantage seemed interesting.

Is there a need to rush 20 Dex or is 18 fine? That way I could take Sharpshooter as my second ASI, the level before I get Extra Attack.

18 is fine if you can easily get advantage which a wood elf and being a rogue is easily accomplished.