I have to assume all this travel is for business or something, correct? So the chances of a companion pass working out well for you in the immediate isn't that great. For the future it might be, but not for your explicit question.

Undoubtedly, the Chase Ink > SWA GC > Purchase tickets will be the most lucrative for what you described. Purchasing ~$7800 in tickets, you'll wind up with nearly 40k UR points, which are much more valuable. You can transfer them right back to Southwest if you are so inclined.

You will also wind up with all the miles your fly on SWA. So at the end of this, you have 40k UR, and (for the sake of example , a 500 mile flight), 22,500 SWA points.


Back to the companion pass. If you have a S.O. or someone with whom you want and will travel a lot, then definitely go for the SWA cards and try for the companion pass. In theory you will get a lot more value out of free trips for your companion than from the points outlined above. BUT, after 45 trips, do you see yourself wanting to fly more (even if for fun)?