Is "Alert" actually worthwhile for high dex characters? Do you actually face a significant amount enemies with dex above 20 or some initiative raising effects? Also I only remember getting "surprised" effect a handful of times - so that second benefit is very situational. Wouldn't a 20 dex rogue win most initiative rolls without the feat anyway?
For Assassin/GS multi certainly it is not worthwhile(you already get a +3 initiative bonus from GS level 3)
"Magic Initiate: Cleric" feat with Bane spell not sounding like such a bad idea. For a pure class rogue durge, but I want opinions.
I know most people barely use Bane because Bless is just a superior use of concentration. But if you already have a cleric casting it(in this case shadowcute), wouldn't it be quite useful and even op to have another character using it?
Rogues usually really have one prime useful action per round(sneak attack). After drinking that speed potion and alpha striking some dude it seems to me like debuffing 3 enemies for 1d4 penalties on saves and attack rolls would be more useful than using the extra action for a meagre attack.
Would pick Thaumathurgy and Blade Ward as cantrips(the first one pretty useful in dialogues, the second situationally good). The feat thematically makes sense for a former cult leader with divine heritage.
You get plenty of concentration options from items. Moderately Armored for Shield equip (and +1 DEX) isn't bad if you're mostly attacking from range. Can use Ensnare shield in melee even. Need to beat saves to make Bane decent and a lot of ways to lose Concentration in any event even without getting hit. Bane is pretty good with Pal/Cleric or if you're getting Bless from heal ring I think.
Bane is a charisma save - many enemies weak on charisma(specially first chapter).
I imagine a 16 wis character will reliably debuff 3 goons in larger battles, potentially bosses and powerful enemies if they have low charisma(i.e: monsters, monstrous humanoids, beasts, etc). Even more reliably if Gale is around casting bless with that Mystra staff which increases spell rolls.
That is my idea anyway. I have a feeling it is such an unused spell that nobody really knows how good or bad it is.