Step 1 will be problematic at every single company I encountered that has a fixed number of vacation days, because they all have a cap on how many you can accum

Step 1 will be problematic at every single company I encountered that has a fixed number of vacation days, because they all have a cap on how many you can accumulate. Which usually is 2 years worth of vacation time (usually 15-20 days per year, so 30-40 days max), after which you cannot accumulate any more and just start losing them. EDIT: I profusely apologize for this comment. It's been a rough morning, and the math didn't check out in my head at first. Step 1 from the parent comment should work just fine with the number of vacation days I listed, since 30 days * 8 hours = 240 hours.