I had my second session with the swordsage last night. Things went better in this one than the first, so the unfamiliarity factor is probably receding. Good enough for me, although the king of the spotlight was undoubtedly someone else.
The first fight was against a half-dozen dragons besieging the giants' fortress. These were size L blacks and H blues... which, against an EL 17 party, is pretty much meat.

The dwarf barbarian is an engine of destruction once he winds up, and the spellcasters chipped in with various boom spells to add to the slaughter.
The SECOND fight ended with us running away, tails between our legs. The dwarf doesn't have a tail, so he substituted his intestines instead. This was against a named fang dragon, buffed to the gills with spells. We dispelled the buffs, but by this time the dwarf had been taken to -50 hit points and was only saved by the PHB2 feat that lets you delay damage/effects suffered to the end of your round. It's like 3/4 of the good bits of the frenzied berserker, without any of the bad bits.
The THIRD fight had us quaking in our boots initially, but ended up being relatively easy -- not that it saved the dwarf from having his guts removed a second time. This was against Brazzemal the red dragon, after we blew up the dracolich phylactery he was looking for. A combination of grasping hand (? the spell that forces a save each round to avoid being stunned), Swooping Dragon Strike and reactive counterspelling meant that he lost quite a few rounds doing nothing, although he still managed to rip the dwarf a new one. I can also confirm that Greater Insightful Strike is very useful for cleaving inanimate objects... such as, I dunno, a phylactery.
The FOURTH fight was part of the next AoW module, taking place in the Wormcrawl Fissure, wherever that is. All I know is that it contains a bunch of kobolds who follow some red dragon called Brazzemal who used to live in some fire giant cave that was too small for him and had 666 gems stuck in his belly or he did before we cut them out, along with his horns which are now adorning the dwarf's helmet. Or something. And chimeras.
Undead chimeras.
Undead chimeras dripping with WORMS THAT EAT YOUR BRAIN!
Undead chimeras... that had the party very happy because their holy undeadbane Kyuss-bane silver weapons dealing an extra 6d6+4 damage per hit could FINALLY be used to full effect. It was a slaughter, and not of the party members. Not that I approved of such one-sided violence, partly because it ran counter to the sense of dread and foreboding that the designers undoubtedly wanted to invoke, but mostly because I didn't have such a weapon. D'OH!
Some people maintain that there is a rich and detailed storyline connecting these random instances of violence, but after careful study, I have come to the conclusion that they were mistaken.
Greater Insightful Strike is now established as my workhorse attack, often in combination with One With Shadow. Even now that I have 5-Shadowcreepingiceenervwhatnot, nothing else deals as much damage in as reliable a fashion. Swooping Dragon Strike runs a close second, tempered only by the desire not to abuse it so much that the DM clamps down. A DC 60 Fort save to avoid being stunned is just stupid, so I've suggested turning it into either dazing or staggering (which is still pretty bad).
The session overall was an interesting contrast with the first one. In the first session we were fighting mostly giants with crap ACs, which I could hit easily even with my middling attack bonus. This time it was dragons with AC in the 40s, and without One With Shadow, I'd have been wasting a big chunk of my strikes. It's been noted that this mirrors the experience of spellcasters, who often have big spell effects contingent on the target failing the save.
I'm finding the per-encounter limit on maneuvers to be quite a major factor in my tactics. While it's true that they refresh after every fight, typically _within_ each fight I was always careful about what to use. This is very different to, say, a sorc who can just blast away with scorching rays every round with impunity. Heck, even a wiz at 17th level has enough spells that running out isn't a concern (you'll run out of hit points before running out of spells, and that's a limit that applies to everybody). I'd say that Adaptive Style refreshing all of a swordsage's maneuvers is necessary, if you don't want them to be ineffectual for half of each combat.
The movement maneuvers (Shadow Hand teleport, Quicksilver Motion) are great for saving one's bacon, with the proviso that they can be used only once. I finished the fight with Brazzemal untouched, save for when I rolled a 1 to save against his Tempest Breath and took 4 points of damage. A good save to roll a 1 for.

I can only imagine how annoying I'd be if I had some of the counters from Setting Sun... probably not that annoying, actually, given they mostly rely on opposed rolls (Str, Dex, attack) and trying that against size L, H and G monsters sounds like a losing proposition.
Plans: assuming I don't get turned into wormfood in the Fissure, I'm intending to get Diamond Nightmare Blade next level. Combined with the true strike I got enchanted into my sword during a momentary lapse of reason from the DM, that should make for some good
cheese smackdown potential -- at the least, it'll reduce my dependence on GIS. I still won't be matching the dwarf for sheer carnage, but since I'm (usually) not risking my entrails in each fight I can't complain.