Conclusion! It ended up being cheapest to spend $20 for him to transfer 2000 points to me (cheaper than me purchasing the same amount for $60). The transfer went through instantly and I was able to get both of our one way tickets for free! Very happy with that.
Now for our return visit, I am very tempted to use Spirit. It is nearly 50% of the price of SWA, even with us paying for luggage.