Kaylon

If you plan to use Gambit effectively your focus should be to ensure you never miss/graze or else you won't get your resources back. You also want to have as much Guile as possible to have close to 100% Hit to Crit. With all that in mind, some key items are the Cap of the Laughingstock, Gauntlets of Accuracy/Gloves of the Dungeon Warden, Ajamuut's Stalking Cloak, Devil of Caroc Breastplate. For weapons the most effective combo, maybe not as sexy as two daggers/stilettos, is Scordeo's Edge & Rust's Poignard. For the other items you want more perception/intellect/beneficial effects duration - Whispers from the Depths ring gives Acute that stacks with other active intellect buffs (like from Ripple Sponge or Potion of Mental Prowess), Strand of Favor, Ooblit. For resting bonus probably the buff from The Abyss (25% beneficial effects duration) is the most useful for you (even more if you plan to use Scordeo's Edge with Blade Cascade).

It's impossible to maintain perfect balance between the damage taken and healing. Use a trickster instead of a streetfighter and if you want to see ripostes get also a shield...

Since you already have a paladin in your party I would go with a trickster/soul blade instead. WotEP does great damage with SA against multiple targets and vs single enemies you can switch to Sun and Moon + Tuotilo's Palm/Best Defense for great dps because you can spam SA.

You should try devoted/monk with Grave Calling/Scordeo's Edge crit build. Very high survivability with long lasting Unbending Trunk (can also use Shroud of the Phantasm to gain more discipline), plenty of wounds, high dps, good CC, etc. For slash immune you can just use your fists. Another fun build is steel garrote/trickster using Voidwheel. The draining ensures you won't die from the self damage of the sword, while delivering huge single target damage, especially when it procs. Of course you can use other weapons or even a shield, depending on the situation.

Corrupting Beauty gives a timed buff aura which applies Distracted in a small area around the player. PS. The Best Defense is great when used with 1h ranged weapons - great procs and also the recovery reduction.

Heartbeat and Blighted Shot are indeed nice for scouts (good HoT and one big shot every fight). Living Wood has 20% to trigger on attack (not hit) and thus Driving Flight changes nothing. It has also a base range of 5m ie around 7m with 20INT - which means you will draw aggro rather easily if you want to hit something with the AoE. Corrupting Beauty is basically useless because it requires to be nearly in melee range to affect something. For Maia, the Red Hand is the best option overall, while for a ranger watcher Frostseeker is also hard to beat. You're basically left with the chanters ands wizards as possible users - overall I think Blightheart is the most suitable for a chanter/rogue build.

If it were other classes maybe you could argue that's because of bashing. But monks use it obviously for the class specific enchantments and because bashing isn't such a big penalty with that shield. Also I doubt the statistics imply that most high level monks use a shield, instead it can also mean they have a shield equipped (as a back up weapon set) and that shield is Tuotilo's Palm.

If bashing shields were so great then most builds would already include Tuotilo's Palm. Defense, dps and enchantments all play a part and bashing isn't the answer for most builds.

I think the mod is great and for me this change is a no brainer - since Tuotilo's Palm is perfectly balanced I see no reason for the other bashing shields to underperform. Some could say that shields without bash would become strictly worse, but I would answer that "Bashing" is a kind of enchantment for shields and, like in the case of weapons, not all enchantments are made equal. Right now, daggers with modal are arguably a better alternative to bashing shields - +10 melee deflection from the beginning (like a superb buckler) while having better damage, penetration and accuracy. Losing +1 engage and the ranged deflection isn't a big deal most of the time.

Turn based is a completely different experience and it is indeed a viable strategy coupled with maxed mouvement speed, however it will increase greatly the length of the fights.

Riposte isn't something you should build around - it's just a little bonus for defensive rogue builds (trickster/soul blade or trickster/steel garrote for example). It's possible however to force misses either using medium shield modal (Nerian's Ward is nice for that), items giving "resistances" (like Humility robes) or immunity to disengagement like Nomad's Brigandine/Gipon's Prudensco.

I don't think it has anything to do with being legit/boring reasons. I see three simple reasons why this interaction remains unknown and is "rediscovered" from time to time: it requires to play without a party - which most people don't do you have to play certain class combinations - most people have already in mind what they want to play and the tactician doesn't come very often (a cipher in the party can cover the needs of brilliant) since the interaction isn't obvious (compared to infinite dot + hiding or brilliant + SoT + BDD which can be easily figured out) and the reasons above, most people don't ask/learn about it If we had a sticky post with all the little exploits/unintended interactions in the game I'm sure people would use them more often because they make some combos more viable and the game more fun.

How do you maintain bloodied/flanked status all the time? Dorudugan has 21 slash AR in potd, I think - I don't see how can you penetrate his armor with Scordeo's Edge even with Windmill Slash activated... Also Vanishing Strike can last maybe 15s with optimized gear/stats thus you can use at most 6 times with Empower. It's hard to believe that Dorudugan can be killed under 90s.

I see the trickster as someone using many "surprises" and illusions, which can translate to procs/effects and illusion spells, combined with a bit of swashbuckling. Ring of Clenched Muscle, The Magnificent Escape Cape, The Left Hand of the Obscured/Gatecrashers/Boltcatchers, Rakhan Field Boots are some good options. For weapons I would equip Kitchen Stove + Modwyr and Whispers of the Endless Paths for their abilities per encounter. For the regular weapons a mix of Scordeo's Edge, Gravecalling and Rust's Poignard works pretty well. For slash/pierce resistant enemies Ball and Chain, Endre's Flog of Obedience and Sungrazer can be used as backup. Besides trickster's spells you could also use traps, poisons, bombs or scrolls to spice things up even more if needed, but the consumables tend to become tedious in the long run.

Using the AI you can try to use "Focus is at maximum" as conditional and use a spell like Mind Blades (which won't be wasted) or one with long casting time (that way you have 2-3s to react before the spell is finished and switch to another spell if needed). After that you have to learn how many spells you can cast during the ascended phase - also finishing with spells with short casting times helps not losing them. However when you can fill your bar in 2-3 shots you stop worrying about these things because you will be ascended most of the time. Attack speed is also very important if you want to increase the number of spells you're able to cast while ascended - Captain's Banquet, Abraham + Contender's armor, dex bonuses/buffs...