I think his point was that there's some unwritten upper bound, like say, 16 weeks. Would be easier to just tell me what the upper bound is, so I can take that, rather than under utilize my vacation days or offend the unwritten rule.
It is a pain in the butt to file paperwork as an employee and do all the accounting as a business. I know of another company that got rid of vacation days for this reason, and it seems nobody regrets it.
Even though one might take comfort in a de jure number of vacation days, frankly, it seems to me that if one exists in a toxic culture when it comes to vacation no amount of policy is likely to make the situation much better. In the pathological case, it gets lost entirely from over-accrual or turned into a cash payout.
Another way to look at the vacation day policies is they are mostly a reflection of the work/vacation culture, not the cause of it. And in that respect, such a strategy makes it harder to evaluate an employer's gestalt attitude towards vacation. Too bad it comes with a bitter pill of accounting work for all involved.
For what it's worth: Heroku is my current and has been for a couple of years, and I take vacation, and have been reminded to do so. I'd say about 25 days/annum. I've not kept count, but I can think to some of the bigger-ticket travel making up most of that, so if there is a mis-estimation it is not vast.
They don't want you to think in terms of "fully utilizing" the vacation days available to you, like you're squeezing vacation days out of the system, trying to take all you can. Take what you need to be happy and productive, then come back. I'm guessing they know this is tricky, even for people trying to be honest, and are trying to make it work anyway.
