Multi-Classing as a Rogue in 5E

[Kool Dud]

So I've been thinking about classes to Multi class in for my rogue, since lets be real here the abilities past level 11 are alright at best. Im currently a 4th level rogue and while its still probably a bit too early for this i thought might as well plan it out now. I would like your thoughts and ideas of what i should multi class in for some fun. im thinking of something that could still dish out a nice amount of damage while still feeling like a rogue and sneaking around the place with all my proficiencies. here are what my stats look like:
4th level Assassin rogue
Health:30
AC:15 (11+Dex Mod)
Str:11
Dex:19
Con:12
Int:12
Wis:16
Chr:16
Proficiency in Acrobatics, slight of hand stealth(+expertise), insight, perception, deception, persuasion, thieves tools(+Expertise),
I also decided for the Alert feat for my ASI rather then uping my Dex since i thought 19 dex was way too high this early on and i was planning on getting the stealth feat from unearthed arcana next anyway, the DM is being kind however and said that i could change my feat as long as its before we hit 5th lvl.
Right now im thinking that i should multi class 11/5/4, rogue fighter, and bard respectively. With this i miss out on Sneak attack and an ASI and i lose my 17th level assassin ability but i think its worth it since while Elusive is good and all i dont think ill miss it and the rogue 20th level is just plain bad. multi-classing like this allows me to get more expertise and jack of all trades from bard swell as some spells and college of lore gives me even more proficiencies if i decide on that college. From fighter i get the extra attack and two weapon fighting style, aswell as action surge and all that fun stuff but im still deciding between champion for the increased crit or battle master for maneuvers. and as a rogue i get reliable talent on the 11th level which is why i decided on bard since jack of all trades works with reliable talent and really everything past reliable talent isnt that good other then the sneak attack bonuses and the one ASI ill miss out on.
So what are your thoughts? should i multi-class into something else? Any ideas or changes you would make to my current idea? we are using unearthed arcana so if you have any ideas that involve it they are welcome. Really i just want to have fun and i thought this would fit what im trying to do which is to deal nice damage but still have all those proficiencies.

[JellyPooga]

If skills are your bag, then you might want to consider Ranger instead of Fighter. Extra skill proficiency, circumstantial Expertise on a grab-bag of skills and an extra attack vs. Multiple foes if you go Hunter, on top of TWF and Extra Attack. Not a bad choice.

[SharkForce]

not sure bard adds that much. +3 (or more likely less since you won't be level 17+ most of the time) to a bunch of skills you didn't think were important enough to learn? that's not that great.

i wouldn't go champion. battlemaster is amazing for a rogue.

the dip that i think would be interesting for skills would be knowledge cleric. the channel divinity gives you proficiency in anything for 10 minutes, and gives you 2 skills (and iirc arcana is used for a number of magical traps). and the moment you gain proficiency, your reliable talent kicks in, which it wouldn't do for jack of all trades. so anything you could possibly need to do, you can suddenly guarantee minimum 10 + proficiency bonus + attribute modifier.

3+ levels in cleric gives you guidance as a cantrip for skill checks, bless to help you land attacks and make saves, sacred flame for radiant damage in case it becomes necessary, and full access to the entire cleric list up to the level of spells you can cast in case of emergencies.

oh, and level 15 in rogue is pretty good imo. 13 and 14 are probably mediocre for you, but 15 is proficiency in wisdom saves, which you want anyways. 12 could easily be proficiency in any 3 skills, since you seem interested in proficiencies.

in any event, i don't think bard is terrible, i just don't think it's as good as other options.

[smcmike]

Two weapon fighting style doesn't make a lot of sense for a rogue, to be honest. You've got better things to do with your bonus action, usually.

[DarkKnightJin]

I'd say to have a good look at Ranger or Cleric.
The Knowledge Domain would be pretty good if you're wanting to be a skill monkey.
If you want some flavor, you could look into the Trickery domain. Pretty sure that Duplicity thing from their Channel Divinity would give you Advantage on your attacks.

[Specter]

In your case, Ranger today, Ranger tomorrow, Ranger forever. You get:

- A bonus skill (and decent ways to use survival abd sneaking);
- A fighting style
- Hunter's Mark (+2d6 every round with TWF, more with Extra Attack)
- Hunter feature (I'd recommend Colossus Slayer, but you may want Horde Breaker)
- Extra Attack
- Pass Without Trace (+10 to stealth speaks for itself; I only mention two spells but there are others just as good)

All of this with five levels.

[JellyPooga]

In your case, Ranger today, Ranger tomorrow, Ranger forever. You get:

- A bonus skill (and decent ways to use survival abd sneaking);
- A fighting style
- Hunter's Mark (+2d6 every round with TWF, more with Extra Attack)
- Hunter feature (I'd recommend Colossus Slayer, but you may want Horde Breaker)
- Extra Attack
- Pass Without Trace (+10 to stealth speaks for itself; I only mention two spells but there are others just as good)

All of this with five levels.

To be fair, you get more or less all this with just three levels, barring Extra Attack and PWT...Ranger is a much underestimated 3-level dip IMO and lends itself to further investment if you want a more intensive multiclass. The extra attack from Horde Breaker is a great boon to a Rogue, who typically struggles to deal with mook mobs, far more than the paltry (compared to his Sneak Attack dice) +1d8 from Colossus Slayer. At least in my experience.

[Degwerks]

Maybe consider Assassin 11 / Hexblade blade pact Warlock 5 / Hunter Ranger 4

Take Thirsting Blade for 2 attacks, Mask of Many Faces for at will Disguise Self, and Eldritch Smite to capitalize on your assassin crits and sneak attacks.

You'll have a Pact Weapon that can never be taken away. Cantrips and 3rd level spell slots that replenish on short rests. Ranger spells and Fighting Style and Horde Breaker or Colossus Slayer.

Hexblade Curse gives you 19-20 crit range and your proficiency bonus on damage rolls.

Eldritch Smite can give you up to +4d8 force damage on a melee attack and knock a huge or smaller opponent prone.

Max level your crit with a shortsword is 16d6 + 8d8 if you use Hex or Hunters Mark.

Use the UA Revised Ranger.