[gruez]

But isn't it better to find a tax avoidance strategy that's mutually beneficial to both sides? Sure, you can ask for an extra $10k that gets taxed down to $5k, but if you can find a creative workaround to get $8k instead for the same $10k, isn't that better than trying to ask them for a $16k raise to make up for the taxes?

[srockets]

That $8k may cost another $5k to implement: current systems used by the would be employer may not be geared up to handle that non-standard asks.

[pdimitar]

Valuable counter-point, thanks. Still their problem though, and they should make it a bit more transparent: "It would cost us extra to implement this, are you OK with a final offer that's yours minus $3k to offset our costs?".

[setr]

I think the best thing is to ask for $10k or equivalent, and then let the HR team come up with a sane way to construct that value that works under their system. It's kind of like getting requirements where the customer tries to tell you the exact logic to program, but since it's not their codebase/background, they end up coming up with convoluted solutions.

Just tell me what you want, and let me as SME figure out how to get you there.