The reason you are not getting much of an answer is because of how complicated the question really is. Generally speaking, extensions are designed for more short term issues involvoing obligated service & needs of the service. There are reasons why a member can choose to extend too.
Mightyz is correct. Usually the extensions are obigated service issues, whether for school, for a transfer, or advancement.
There used to be a max extension period of 6 years per contract. You don't want to get into a situation where you want to negotiate, and you are the one over the barrel because in order to stay, you must re-enlist for a minimum amount of time. If you are in a rate that has bonus potential, and you have to re-enlist for 4 years minimum (I don't know if that's still true), and a bonus comes out, you won't be eligible for that until your 4 years is up. However, if you were on an extension and a bonus came up, there is usually a window for people to re-enlist early for a longer period of time for the bonus, when it's about to be dropped. The time you were already obligated for won't count, but the new time added on will.
Every case is different, and you don't want surprises! Sometimes, it doesn't really matter, for instance, if you are beyond bonus realm. Check with your YN or Command Chief to see how it applies to you. They can make sure you have the most current info.
I strongly suggest reading the Pers Manual yourself to understand everything. I'm sure rules have changed since my retirement, but early in my career a YN assured me that my 2 year extention for a schoold did not count as a re-enlistment. Thus I lost $10,000 (a lot of money way back then) when I did my first reenlistment. My new rate had a VRB (variable reenlistment bonus) and my old one did not. But the 2 year extension counted as a re-enlistment. That was a 10k lesson I learned and I never forgot it.....Regards.....Bill
From what I understood from a recent personnel issue we have at my unit, almost all extensions are being approved. I know a handful of people who are extending a year so they can wait out the probable SRB.
Back when I wanted to retire in '05, EPM had me extend for 4 months due to replacement not being able to relieve me- so I extended for 4 months and took 3 months leave later in the year- I at 1st thought it was stupid but, in the end it worked out for me anyway. Better job and started it 30 days into terminal leave.