MOST won't cash it!
Believe me, MOST of the figure skaters won't be able to cash in on their medals.
First of all, there is the obsession with the gold medal, with so many acting like silver and bronze medals are completely meaningless.
The number one reason that most figure skaters won't be able to cash in on their medals, unless they are gold medal media darlings, is that professional skating is almost dead. In the big excitement that came over the skating world because of the Tonya-Nancy happenings and the Maya-Pasha-Evgeny-Sasha Z. soap opera-like tales, there was suddenly skating almost all the time!
There were so many shows on tv, and it was great. However, almost all of them have since disappeared, and most of the traveling ice shows are in big trouble, having to cancel many shows because of lack of ticket sales (They might try reducing their prices). I guess that most skaters will have to go into coaching to try to make a long-term living in the business, or go into something related, such as designing skating costumes.