I ride alone frequently... And I've also gone over the side a few times. Boy Scout, Middle Merrill, SART...
@bigringrider101 was right behind me for that last one. As I was hanging onto the bush, I remember him saying, "Wow, that was an easy stretch of trail. How'd you end up down there?"
I miss Berni...
When I ride alone, I ride differently. I smell the roses more, and set my own pace... There are quite a few features on the front range that I'll clean when others are around, but walk when I'm alone. Or... I don't put the same effort and value into cleaning them. The risk isn't worth it when help might be a long time in coming. But... I would never completely skip a trail because of the risk or the difficulty level...
The level of risk that is acceptabele for you is something you have to figure out for yourself. I would just advise to look for a middle ground... And it doesn't hurt to have a guide the first few times. When you're ready to go up higher on the front range, let me know...