We just released an update to the "Play Random Track" algorithm to source from all tracks (opposed to top 500 trending which is what it was doing previously) and excludes your most recently played 20 tracks (we will increase that from 20 to give better freshness to tracks shortly). We also added a new "Shuffle" tracks listing based on the popularity of "Random Track". This should help surface more of the +10k Free Rider tracks currently on FRHD. Let us know if you see any issues with the latest update.
We will have a wireframe for feedback this week. Our goal is to get a workable version to the site this month, ground has broken on the editor we will have a better timeline once we get into it a bit.
Current tracks on FRHD are 1000s of the most popular from the community over the years, so chances are you will play a "popular" track on random.