I think from people I know with a "Can you spell that?" name, it isn't the obviously tricky ones that are the real PITA.
The really unusual ones tend to get a 'How do you say that?' but the ones that you'd expect to be easier tend to get said all sorts of ways.
I have a fairly unusual welsh name and people will try to make it into something they'll recognise, or they'll ask me to say it then repeat it making it sound horrible, or they'll say something like 'How the f**k do you say that?'. My name gets misspelt a lot. I also get told things like 'Why do you say your name is [My real first name] when it's really [Another name], and 'I know how to spell it' (no you don't)
A friend called Ceri has what I'd have thought was a much easier name, but she gets Serri, Surrey, Cherry, Cherie and Cerise and if they've heard it but not seen it written down, Kerry, Kerrie or Keri
I often work with people from different countries, and it's the monoglots who struggle with my name. Having said that, I struggle to remember to say their names correctly, usually because I first heard an anglicised version - something like 'Oh you'll be working with Jürgen and Liisa' and they aren't 'Yerg-en' and 'Lisa'