I went to school with a boy called Kit. Artemis is cool. Bliss and Hero are not my cup of tea at all.
None of those names would make me think negatively about the parents at all. I don't think the names are too unusual or that the children would be teased, either...not even a boy "Jess". I'd probably think the Mom was well-read or well-educated and creative, and also that she wasn't trying to hard to come up with something too unusual or different or "out-there".
Oswin Rose - okay, I sorta like it
Artemis - okay, unusual but not crazy. Artemis Quinn
Hero - this one is a no go for me. It's too much of a word and the masculine form of the word at that. I would think that the parents were trying to ignore reality and be super hipster and "intelligentsia". I can see it as a middle name
Eliza - meh, popular, but not my cup of tea, it's okay
Posy - not too fond, it's okay, I think I'd prefer it as a nn for something like Persephone, Portia, Primrose, Priscilla, etc.
Bliss - bit too much branding for a name--sorta like using Sexy, Foxy, Happy, Silly, Pleasing, etc as a name.
Milo - great, nice name
Jess - I think Jess is fine on a boy, not sure that I'd use it as a stand alone but I think it would work fine. Could work as a nn for James, Jasper, Jefferson, Jones, Joseph, Justice, etc.
Kit - again, I probably wouldn't use it on it's own, but as a nn I think it's great. Would work as a nn for: K/Carter, Christian, Clayton, Clifton, K/Colton, K/Constantine, K/Curtis, C/Karsten, Keaton, Kenton, Kristof
Thomas - fine, great name
Samuel - fine
Wesley - I actually really like this one. I think it's underused and very nice. Definitely more safe than other options, but a good name.
Oswin Rose: Oswin is strange strange and I strongly dislike it. Rose is a pretty mn.
Artemis (no middle name here yet, open to suggestions). Strange!!
Hero- not a name, it's like when people name there child chastity. i think uhhhhhh.
Safe Girl List:
Eliza love, in my top 3.
Posy ok, nms, would be in a dream list to me not a safe list if I liked it.
Bliss strange, like hero. maybe for a mn.
Dream Boy List:
Milo i think it is a great name! not too out there at all and I am pretty conservative with names.
Jess I think in the 80s this would've been okay but now adays seems to girly. My sil's name.
Kit -my friend named her daughter this and the name of one of the girls in the movie "A League of their Own". I actually love this name for a girl, way too feminine for a boy.
Safe Boy List:
Samuel-love, in my top 2, but I hate that so many people also name their dogs this.
Wesley-not my fave, boring to me.
I love Artemis!! I think Eliza goes well with it: Artemis Eliza or Eliza Artemis.
From your boy's list, I have always loved Thomas... Milo Thomas or Thomas Milo perhaps
Dream Girl List:
Oswin Rose - I really REALLY like girls' names that end in -wen. Anwen, Lilwen, Rhoswen. So while Oswin doesn't particular do it for me, I like the overall feel. I don't watch Dr. Who or know anything about it.
Artemis - I love Artemis and Artemisia
Hero - Dislike. A lot. And I love a lot of Shakespearean names, but I just cannot. Viola Oswin would be swoonworthy though.
Eliza - Love
Posy - Feels cutesy. It's adorable actually but its very tiny girl or old lady to me. I imagine it as a nickname. Mariposa? Josephine?
Bliss - Way wackier than Artemis. And not as nice as Blythe.
Dream Boy List:
Milo - Not dream-weird at all. It's not my style but its pretty on trend. If you love it I have no idea why it wouldn't be usable. I just don't like it and prefer Miles, same as I prefer Hugh to Hugo, sorry.
Jess - Usable, but prefer Jesse.
Kit - Makes me think of Kit Carson in terms of males named Kit. In fact I'd toy with using Carson as the formal form, but I am a history nerd. I like Kit, but my true love for it is Katharine. Sorry.
Safe Boy List:
Thomas - Hate it. Sorry. Thomas wigs me out. Please use Jess or Kit instead. Most people don't hate it nearly as much as I do though so its sorta safe.
Samuel - It's fine. I prefer Samson but that might be as weird as anything on your dream list. Nothing's really wrong with Samuel.
Wesley - No more normal than Milo, and no nicer either. The only W name that's normal-ish that I like for a boy is Wyatt.
I actually named my daughter Oswin Rose, so I approve of that name. ;) I get a lot of compliments on her name, but I'm constantly being asked to spell it and people ask if it's a family name, which leads me into long explanations. Very few people have made the Dr. Who connection.
I just wanted to stand up for Hero as a name for a girl. I think I like it because of its similarity to Hera, which I really, really like. I also think Hero is fine for a girl and not necessarily masculine. I heard American linguists recently say that American English is moving away from gender specific nouns. "Actors" now mean both men and women quite commonly. We can have a master of ceremonies that is a woman. In the same vein, I don't think that we need to absolutely specify a female hero as a heroine.
I really like all of these names-- I especially love the name Artemis. I always love Greek names, and have thought a lot about using Athena or its Roman counterpart, Minerva. The only name I feel a bit weird about giving to a boy is Kit because it's been a name I've always loved on a little girl. I think Jess on a little boy could be really cute.
I like Oswin and Milo, but the rest I really don't like at all. Especially Jess and Kit for boys. They just seem WAY too feminine to me. That's like a step below naming your son Jessica. I do really like Jesse, though. Artemis and Hero I just think are weird.