Couple of more.

I retire from AF on 1 Sep and went to indoc on 2 June. Starting last Fall, I requested a retirement eligibility check from AFPC every 3-4 weeks since it takes them 2 weeks to respond yes and then you have about 2 weeks to request that date officially or it expires. I did this while I interviewed and waited for a class date (Jan-March) so that I could always put in for immediate retirement on my terms if a last minute deployment dropped. Finally in mid March I picked 1 Oct as my retirement date hoping for a July Delta class and finalized the retirement request and got my retirement orders. When Delta offered me a June class in late April, I asked AFPC to change my date to 1 Sep and it took about 10 days to get that changed/approved. Only hold up was commander had to submit in writing that he understood he would not get a backfill for approving my earlier retirement.

Depending on your rank/years of service, don't assume that selling back your leave is a bad deal. If you add your retired pay for the month to the sell back amount many times it's close to a wash. In my case if you added housing and flight pay together it was pretty much the same but you also have to consider the tax implications because your BAH is not taxed (but your retirement and leave will be).

Also, if you do the JAG brief, they will brief that you cannot use permissive TDY to start a new job. Not sure anyone would call you on this but something to think about. I went to indoc on normal leave to avoid this and signed out of the AF the day after I finished. I also had to sell back some of my leave.

AFPC site says they want min of 120 days from day of request until you sign out (start terminal or permissive) but I gave them less than 90 on the first request and about 40 days on the change to 1 Sep and never got any push back.

Having your commander on board is key to having this type of flexibility.

Overall--there are angles to be worked if you do your homework and have leadership buy in.