Employers may deem that a cash-out feature meets their vacation strategy. Strategy considerations include:

* Allowing employees the flexibility to buy and sell to accommodate vacation plans that can change over the course of an entire plan year.
* Designing the plan to support employees who get sick and need PTO while still rewarding those who do not use it by buying back unused time.
* Encouraging cash-out of unused PTO to be applied to other benefits areas, such as retirement accounts.
* Providing the possibility of getting extra pay at the end of the year and of not risking forfeiture of vacation or cash benefits encourages employees to use the benefit.

When using a cash-out strategy, some employers reimburse sold PTO days on a dollar-for-dollar basis, whereas others apply a reduced rate (e.g., 50 cents on the dollar). Also, consider how cash-out values will be determined for pay out—at the original purchase rate or based on the employee's compensation when the cash-out occurs.

When you are old and sitting in a retirement home will you ever say "I'm glad that instead of using my vacation time I went to work!"?

I've been at my current job long enough where I have a large annual allotment. Many people find it tough to take all their time since we have a generous policy. A few tips that work great for burning days in a constructive manner.

-Take some Fridays in the summer off. Shorter work week and nice long weekend. You'll thank me.
-Take the week of Thanksgiving off. For most folks, that only requires three PTO days, and you are off for nine.
-Take the week between Xmas and New Years off. It is always quiet with so many people taking time off. So those days in the office go by super slow.

Also, anyone who can leave the Midwest for a week in January or February and chooses not to is making a mistake.

That sounds like a terrible time to leave town. Give me all the Christmas parties, drinks, lights, craft shows,etc. And then give me more.