I'm in pretty much the same boat, just a little closer on the timeline. Retire in March (21 yrs); terminal leave etc. starts in January. From what I gather at TAP, they used to issue a preliminary DD214 upon checkout (terminal leave), then the "official" one after the actual retirement date. For whatever reason, they recently stopped doing that.
The recruiters I've talked to have given various answers on the question. Some seem very familiar with the military/terminal leave situation and say a statement of service or even a copy of the third retirement message from the bureau (basically a SOS in itself) will suffice. Others say no joy 'til the actual DD214 is in hand. A couple wouldn't even consider hiring while on terminal - had to wait 'til after the retirement date.
Originally planned to knock out the CDL school and company training period while on terminal for $$ reasons. Decided to do the school on terminal (graduate a week before retirement date), get the DD214, new ID's, etc. upon retirement, then do the orientation/training period. That way I don't have to sweat getting back to a base for retired ID cards, wait for DD214 via "snail mail", etc.
Best of Luck
Rick