My question is, will players tell you that they won't accept a new contract entering the final year of Arbitration?  I had a couple guys who completed arbitration, and then wanted to go to FA.  However, will that ever happen entering the final year of Arbitration, that they simply want the arbitration, and then to go FA?  To hedge, I am contemplating going 5 years in the 2nd year of Arbitration (which yes, I know makes players more expensive in the short term).  I just don't want to find out the hard way.  If you all believe that what I describe won't happen, then I won't.

Remember, the question is entering the last year of arbitration, not following it (Free Agency year)

Any time you take a player through arbitration three times, there is a risk that he will not be willing to negotiate with you in his FA year.  You have no way of knowing for sure if he will or not.  

Your best bet is to assume that he will, and if he's somebody you want to keep long term, offer him the LT contract rather than arb him in that third year.

I understand that - my question is there any risk that at the point of the final arbitration year, he would prefer the arbitration to the LT contract so that he can become a FA filling that season.

Ok sir, that's what I needed to know. Thanks