Any insight on how to optimize this multiclass? I'm relatively new to D&D, but have really enjoyed the experience! Flipping through the Players Handbook, I stumbled upon an idea about a character I want to build. For lore I believe the Changeling to be the race I like, +2 Charisma goes well with SB and spending the +1 in Dex provides synergy with the needed 13 in Dex to multiclass. I imagine going 9 in SB and 11 in HW. My thinking is the combination of sneak attack, rakish audacity, extra attack(s), planar warrior, and distant strike for the ability to apply damage and blink from one enemy to another, seems like great fun!

My concerns lie in the uncertainty of which class to begin with and at what point to multiclass for best optimization🤔.

Again, any insight or educational advice would be greatly appreciated. Thanks

I’m not an optimizer but I would start SB for 3 levels and then HW 5 to get extra attack. Then back to Rogue to get evasion.

You could easily flip those if you want the extra attack as soon as possible and get your first ASI, but then you delay the sneak attack, fancy footwork, and rakish audacity. 

I’m sure some others would have better ideas for the progression but I like starting rogue for the skill choices and expertise. 

I appreciate the comment friend! I see your point in getting the 3 lvls in SB first. Makes good sense to get the early perks and then go for the extra attack. I would really like to get distant strike asap, but it being at lvl 11 has me thinking I wont see it until im lvl 14 or lvl15. Either way, I believe there to be enough synergy for the style of play im looking for with the early perks, that having distant strike at lvl 14 or lvl 15 would replace the later level perks that ill miss for multi-classing.

Thanks again for your input! 

If Distant Strike is what you are looking forward to, it might be in your best interest to go straight HW and skip the multiclass unless there is something you really like about Swashbuckler. Sure, sneak attack is nice, 2d6, but your HW gives you a bonus 1d8 force damage, although it uses your bonus action.

Swashbuckler does give you mobility, being able to move without an OA from an enemy if you attack them first, you could use your movement to go to another target for a second attack (after 5th level ranger extra attack). It's not quite blinking from one target to the next, but you could kind of RP it like you move so fast it's almost like that effect, as long as it conforms to all the other rules for the actual movement, you DM might be ok with it. So you are not actually teleporting, but RPing it kind of like you are. 

And getting the extra option to gain sneak attack and adding CHA to initiative is nice, but you can take the Alert feat to gain +5 to initiative, in it's place, if you don't MC.

Mmm, I see your point. I also noticed that the Ranger requires 13 in Wis and not 13 in Dex as I previously had seen. Originally, I thought about a Kalashtar as a HW that struggles with a quori that plagues their mind. What intrigued me about the SW/HW multi-class was mostly for the RP and to add some flavor to the experience. I may need to venture into another direction (multi-class wise) to get a more optimal build.