Decided to have more fun with this cute crossover, there is still more sketches that need to be finished.
1) I can imagine Stitch having the time of his life with Toothless, both feeling they have something in common. Perhaps Stitch is Toothless's reincarnation, who knows. But they know there is something that just feels like a connection, between the two.
2) I don't think Astrid would like Lilo, especially now that Hiccup is always at her side since her sudden arrival to the village. Believing Lilo is trying to get in between her and Hiccups relationship, she would threatened her to stay away. Of course, it might prove difficult with Lilo's close companion always there to protect her.
3) Both Hiccup and Lilo are always eager to learn from one another, and I can imagine them sharing about their many adventures they've gone through. Hiccup talking about the different dragons he's discovered, and befriended, and Lilo talking about all the cousins both her and Stitch had saved from Hamsterviel and found their homes they belong, and battles in space.
4) Hiccup always has to be teaching his people how to earn a Dragons trust, but I believe Lilo won't have such a difficult time like the others. With Lilo's years of experience in bonding with Jumba's experiments, it proves to be an easy task for her, especially with toothless. Lilo's not sure why, but there is something about toothless that makes her feel so connected to him, and also reminds her of someone, but...who?
visit my previous drawing
if interested in this crossover's backstory.