D&D 5E Rogues (melee-based) & Two-Weapon Fighting: Why not always do it?

Ummm... What?

18 strength (requires a 1 level dip in 3.5 or Half Orc in PF) lets you deal 2d6+6 damage vs 1d8+ sod all with weapon finesse. YOu have dexterity as your secondary stat and buff it every chance you can. If you get a cleave attack you can sneak attack again.

My last PF PC was a Barb1/Rogue3 core book only was allowed. 4d6+6 damage hurts a lot at level 4.
 

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A 13th-level Arcane Trickster can use a bonus action to tickle an enemy with mage hand and get advantage on their attack roll. It's a really great alternative to dual-wielding especially if you have a single magic weapon or poisoned weapon or something. Even a single advantaged attack with a rapier seems at least as good as two regular attacks with a short sword, one of which gets no Dex bonus to damage.
 

I using a 2 Handed Sword with a Assassin, seen nothing in the rules to stop it
Friends of mine said that only daggers could be used for assassination (in 1e and 2e)

In 1E you had to use thief weapons to backstab, 2E you could use any weapon you were proficient in. In theory in 2E you could back stab for 260 damage using a lance on a large creature, double damage on a chargewith 18/00 strength and weapon specialization+ magic weapon bonus or more via a girdle of giant strength.Without magic items.

3d6+6 strength+2 weapon spec X5 backstab X2 charging. = 260. You need a dual class fighter/thief RAW with 18/00 and probably invisibility+silence spell+warhorse/mount..
 
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