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These are not at all the associations that I have with either name.

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I like Philip, but I don't really care for Pip. I genuinely doubt that "pimp" would be the immediate association, though.

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I don't really care for Amos. Maybe it's just me, but I'd sooner associate Amos with "Famous Amos" than "Amos Anus."

I don't think Pip was ever much of a thing in the US, no more than Pippa was. It comes off as very faux-British, and also trying way too hard to be ... cute, puckish, in a very Brit-lit kind of way. (Same for Pippa, but it's more like the bizarre-hats-at-horse-races-and-yachting-parties-with-people-called-Wiffy-and-Bonzo. The pimp thing doesn't even come in to it, I don't think.

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Amos is very tempting to make fun of once kids learn about the excretory system. (I wouldn't think Angus would so much, except I have twice seen signs in restaurants advertising an Anus Burger. I wish I was making them up.) To me, Amos also has a whiff of ... blackface about it, because of the old-time radio and TV show Amos n Andy, who at least on the radio were done by white actors doing very stereotypical and offensive-by-modern-standards dialect. It's before kids' time, and mine and yours, but it feels almost on a par with Jemima; a perfectly reasonable Bible name with too much racial baggage. (It also has a strong Amish or Mennonite feel to it.)

Pip may be called a “pimp,” but I don’t think that should alter you. Regardless, I much prefer Phillip (this spelling) with the nickname “Phill” or “Phil”. It’s solely because of how it sounds.

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Amos reminds me of Famous Amos chocolate chip cookies. I do think that Amos sounds close to the anus, but I wouldn’t let that alter you either. Out of the two, I’d pick Amos if I had to.

I don't think Pip/pimp would occur to me unless pointed out. I do think Amos and anus might be problematic, though.

You are overthinking, Philip and Amos are kind of great, and there is no reason the family nn cant be Pip, doubt any one would make a connection to pimp, at least not until well aftwr he can deal with it. The Amos I know has never had any issues at all with the name.

I've known a few Philip people, and they've all answered to Phil. And all the Philippa people have been Pippa. So a boy Pip would surprise me, Great Expectations or not!

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I wouldn't expect a body-part issue with Amos: when kids are at the stage of finding body parts comical, they tend not to use the anatomical term: Willy would be much more likely to attract their attention. What I would expect would be shortening Amos to Amy ... that would give naughty kids a lot of pleasure.