Sgt Stelly,
It is hard to give any further insight on your actual out date. Much will depend on your outprocessing and your local command policies, in addition to any leave or PTDY you take. But it does not seem unreasonable that if you wanted to be out sooner, you could do it in 30 days.
No, DLA is not authorized for moves to Home of Record or Place Entered Active Duty:
Joint Federal Travel Regulation, Chapter 5, Part G:
"
C.
Special Categories DLA Not Authorized. DLA is
not authorized ICW a PCS:
1. From home or from PLEAD to first PDS unless the dependents actually move from the member’s residence to the PDS or designated place ICW the PCS (if the dependents do not relocate to the new PDS, or the member has no dependents, DLA is not authorized from home or PLEAD to the first PDS);
2. From last PDS to home or to the PLEAD;
3. From last PDS in one period of service to first PDS in another period of service when there was no ordered PCS between those stations; "
As far as when your pay hits, you are not able to collect pay until the month after your last regular military pay. So, if things hit well, you could possibly get it the first month after you retire, though it may be longer if DFAS does not process your pay change in time.
Best of luck, and I hope your move and transition goes smoothly.
