I ride year round all weather and have only one bike. It was a commuterized hybrid until recently, but I'm switching to a Surly LHT build this weekend. Given the amount of $ I've saved up and invested in the LHT build over time, I could have bought a couple decent entry-levelish or used bikes for sure of different types.
For my riding, though, this one bike meets all my needs and uses for now. I gave the bare frame a good internal rustproofing treatment the other night, and I plan to get studded tires b4 next winter, so that even the handful of days I miss in a given winter for ice will no longer be.