Yessss....just logged in to my account and I now have my companion pass. So just to summarize my situation and experience once and for all...
I was about 13.4k points short of my companion pass when I checked on Dec 15. I knew I would get about 8.6k points when my credit card points would hit my account toward the end of the month, so I figured I would need about 4.8k points from some other source. I did some research and it seemed like the cheapest (not necessarily the fastest) way to get those last 5k points would be through Southwesthotels.com
I booked my room through the Southwesthotels.com and stayed 1 night checking in Saturday Dec 22 and checking out Sunday Dec 23, which would earn me 5000 points - cost me roughly $200, which is FAR less than flying Business Select for 12x points - but also a bit of a gamble, as my hotel points would have to post by Dec. 31 to qualify for my CP.
My credit card points hit my account on Christmas Day Dec 25, which was expected. I logged in to my account today Wednesday Dec 26 and my hotel points were also in my account and I have officially qualified for my companion pass. I read on this (and other forums) that the hotel points normally will be in your account 3-5 days after your checkout date and those people seem to be right. The T&C say expect the points in your account 6-8 WEEKS after check out date, I assume that is some CYA by the travel portal - all in all, my experience was fantastic and reaffirms why I love Southwest!
In any event, that summarizes my experience - thanks to all who posted suggestions and I hope this helps others in the future.
