Like all the other next-gen kids, he's a blank slate, so it's easy to imagine him having a personality suitable for any house (though with Ron's apparent prejudice -- still! -- against Slytherins, I think he'd beg the Hat not to put him there).
It has been speculated that his sister, Rose, has a good chance of making Ravenclaw? Is Hugo a sure shot for Gryffindor, or can you see him in any other house? If so, which?
Fanfic always seems to depict Rose as the bookish one who takes after her mother, while Hugo takes after his father, but it could be the other way around -- maybe Hugo will be the clever boy with his nose always in a book, while Rose is the one constantly looking for adventure.
I think he'd be pressured by his father to "make him proud," and his mother to "study hard and get good grades." So Gryffindor and Ravenclaw seem the most obvious candidates, but it all depends on how he develops as in individual. Maybe he'll be a friendly, warm kid who shocks both his parents when he gets sorted into Hufflepuff.
Why assume his sister is the bookish one?
Do you think he is the Weasley who lives and loves for Quidditch, or would he be more bookish, like his sister?
I never got the impression Ron was Quidditch-crazy so much as he was desirous of standing out and being admired, and Quidditch was the way to do it. So Hugo and Rose will have grown up with Quidditch talk (and might be influenced by Ron's reminiscing about his days as a Keeper), but they may or may not be Quidditch-crazy themselves.
He'll get lots of lectures from Hermione on how to respect women, that's for sure!
How do you believe he gets along with his sister? How do you believe he parents treat him, seeing as his is the youngest and their only son?
I think Ron will dote on him, and be more likely to spoil him. Hermione will have higher expectations (much as she loves Ron, I can see her trying to nip in the bud some of Ron's habits if she sees them developing in Hugo). He and Lily will probably get along because their parents will encourage it, but who knows -- the dynamic between siblings is always uncertain.
Depends on who makes the biggest impression with him. His dad will certainly influence him, of course, but I can easily imagine the family going in vacation to visit Charlie, and Hugo deciding that his dragon-wrangling uncle is the coolest person in the world.
What could be some possible traits for Hugo personality wise? What reletive of the Wealsey family do you believe he takes after: Book-smart Bill, Dare-Devil Charlie, or Catch-up Ron?
With the constant presence of lots of aunts, uncles, and cousins, Hugo might find himself struggling to stand out (especially since he's yet another male Weasley). He might inherit some of Ron's feelings of being the forgotten one, the one overshadowed by his war-hero parents and aunts and uncles, and his more interesting cousins. (Teddy is a metamorph! Victoire is part-Veela! James, Albus, and Lily, well, they're the children of the most famous wizard in the world! And Hugo is... another Weasley. I can see him feeling that way.)