I think you are much more likely to have packet loss issues on the WAN side of your pfSense than the LAN side.
Any path with a substantial number of hops on the public internet is likely to include a number of hops which are substantially oversubscribed (that is the hop bandwidth is insufficient for all potential users to be able to be able to obtain their maximum bandwidth). Hence packet loss can be seen in periods of substantial demand.
pfSense keeps some graphs of link "quality" in Status -> RRD Graphs, click on Quality tab and use the pull down to select the appropriate interface. If you have your system configured correctly the graph will give you an indication of congestion on the link to the other end of the VPN. There are probably periods of low ping response times and high response times (indicating congestion). Do the periods of high response times correspond solely to the times of file transfer?
Some things you could try. Do some tests to better understand how tweaking parameters affects the outcome..
1. Do you transfer a number of files concurrently? Reduce the degree of concurrency.
2. Convert WAV files to a compressed audio format and transfer the compressed files.
3. Do the transfers outside "busy" times.
4. Reduce the TCP window size used in the file transfers.
What are your requirements/constraints? Must get all transfers (each a multi gigabyte transfer) to complete simultaneously in under 30s in network peak times and incur no additional costs? :-)