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Message: <blockquote data-quote="Pauln6" data-source="post: 6718985" data-attributes="member: 6777422">I think when you convert a PC the issue is the core rather than the class.  Having said that, my PC started as a human rogue and then changed to a wizard at level 3 using the 1e dual classing and 1e UA 0-level wizard rules.  She converted to a shadow mage channeller (modified illusionist) when 2e spells and magic came out and then sorcerer in 3e.  Unfortunately, multiclassing and limits on spell choices for sorcerers meant that the concept suffered a bit in 2e.  When Tome of Magic came out, she multiclassed into shadowcaster with noctumancer prestige class but it was a bit of a messy build, lacking in higher level spells.4e warlock allowed a fair bit of leeway in re-skinning compared to the other classes initially and then hybridded with assassin for more shadowy spells when that was released later.  Re-skinned as a shadar-kai for a bit more of the 2e shadow mage feel.  I was not a huge fan of the button-pushing feel of 4e powers but generally I enjoyed this version.The problem with the 5e shadow monk is that her stats (Dex15, Wis13) don't really lend themselves to a decent monk build, progression as a monk will limit spell-casting, and she has traditionally used a sword (rapier since 4e).  I went arcane trickster to preserve some of the illusion and stealth theme.  She just needs a couple of shadowy spells to top off the flavour I think.</blockquote>