We also started with a smaller, simpler boat. It was great for learning how to sail, and how to live together in a tiny space. For learning systems? Not so much; that small boat didn't have a stove, hot water shower, fridge, heat, autopilot, windlass, etc etc.
I'd support the idea of a liveaboard learn-to-cruise vacation if you can afford it - lots of knowledge and a great chance to test the lifestyle. I'm less sanguine about crewing on a raceboat. Primarily, because when you're racing, you are trying to sail fast and willing to accept a certain level of risk/wear and tear to the equipment, and discomfort to the crew and the point of sail. When you're cruising, your comfort is weighted much higher and your whole style is different. You may go slower, or motor to a destination. And it'll be a different kind of boat, again, a lot more systems.
We saw a surprising number of "HuntAlinaTeaus" (the modern, almost interchangeable-looking production boats, not traditional bluewater boats) in the Bahamas and Virgins. So if that's the area you're thinking, you might be okay with that type of boat; you don't need the super-rugged ocean-crossing vessel. Really, you've only got a couple days passage at most, so you're not sailing out of the range of the weather report, and if you pick your weather carefully you can do it in a range of boats. My point is not to worry so much about getting the ultimate boat right off the bat, get a boat for now, and you can change to a more oceangoing one later on if your dreams send you across the pacific, say.
Don't know if that helps much, but welcome, anyway.