Tigerstar the kittypet.

None of those ShadowClan cats are kittypets, they're loners/rogues. Sasha was a rogue, his kits are half-rogue, not half-kittypet. Tigerstar's hatred was against kittypets as his father became one and Thistleclaw encouraged him to hate them, he never had an issue with rogues given just how much he worked alongside them.

That's not hypocritical, loners/rogues are seen differently to kittypets as they also generally dislike Twolegs or at least don't give in to the cushy life a kittypet lives.

True, my bad. I haven't read that manga in almost a decade, heh. In that case, he's a hypocrite, but also it is his decision. When it comes to Pinestar and Firestar, he didn't have any choice in them becoming either a kittypet or a warrior. Tigerclaw obviously would not have agreed to Firepaw joining ThunderClan, but he had the choice of whether or not to accept Sasha despite her past. Typically we see this in the series anyway: if he makes the choice, it doesn't matter if he insults others over making the same choice (can't remember the specific scene but in book 2 or 3 he decides something that Fireheart is surprised about, and also when Brokenstar is in the ThunderClan camp, Fireheart notes that he's settled down with Brokenstar and sharing tongues with him, despite obviously hating him, because Tigerclaw made the choice to do this).

I believe he passes over Sasha's kittypet past unlike Firestar's simply because he made the choice to mate with her, and made the choice to visit her, whereas he had no choice with Firestar. Further, Firestar gave plenty of reason for Tigerclaw to hate him other than where he came from, whereas Sasha did not - she could already hunt and fight, Firestar couldn't. Same with Cloudtail, Tigerclaw thought very little of him because he was a kit and even though he had barely lived with Twolegs, he was seen as useless.

I wouldn't exactly say he wished him good luck.
He holds the kittypet past against him a lot before Firepaw starts investigating.
His bullying just becomes more pronounced as it goes on.
Even in the middle of a meeting, he is one of the only cats to use this jibe.

Of all the cats who call him 'kittypet', Tigerclaw uses it the most, followed by Darkstripe and Longtail, then Dustpaw and Sandpaw. Graypaw only uses it in speaking to Firepaw or explaining things. Tigerclaw ALWAYS uses it as an insult. The first reaction is the only one in which he doesn't insult him directly - and then, barely.