Hate it for you .......but IME (having lost a few and found many) this is what my guess would be........

You didn' t hit where you think you did ! A qtr away animal hit behind the shoulder and hitting the opposite shoulder is an almost garanteed quick kill.....that I doubt the deer would make it much over 100 yrds.
I wasn' t there but......could you have hit the shoulder on the entry and didn' t get the penetration to the other shoulder that you think you did ?
Maybe you hit behind the shoulder and out through the neck causing a single lung hit ???
I have learned from the few I have lost that if one goes over 100-125 yrds max......to back off and wait......cause more than likely it wasn' t an immediately fatal hit.
If you did hit it good and you ran out of blood at 150 yrds .....I think the deer would have been in short distance of where your last sign was......although they seem to disappear.....he would' ve been there somewhere !! Good Luck the rest of the season !!