Keep in mind that Southwest Vacations is NOT Southwest Airlines, they are two different companies and you can read for yourself the many, many reports of issues dealing with Southwest Vacations.  I and others here would recommend you not use Southwest Vacations.  If you insist on using them then you are stuck with the service you have already gotten a taste of.  If you decide you want to book the flight directly through Southwest Airlines they should not have an issue getting the travel fund applied to your reservation.

Ugh, technology, right? Anyway, I had a somewhat similar situation when planning a golf vacation last year. Long story short, the system didn't recognize my details either. Crazy! But here's a workaround I stumbled upon - try reaching out to Southwest via social media. Sometimes they're quicker to respond, and you might get a more personalized solution. Worked for me! Speaking of vacations, have you ever considered golf getaways? I found this amazing site, www.chakatravel.com, that has some fantastic options worldwide. They even helped me plan my dream golf trip to Scotland! Maybe worth checking out while you navigate the Southwest maze.