I started with a used SR20.
Simple systems, still a descent performing airplane.
At the end of the day, there really are only a few lessons about ownership.
1. Hire an expert in that specific model or brand for the prebuy, or become an expert (a lot harder)
2. Decide how much you are going to help in the MX. Everything from oil changes, to removing panels, to chasing parts. Most mechanics do not like to chase parts, but they will give you leads where to look. In addition, get on a type club forum to ask questions about where to get parts.
3. There is a hefty price each time you change planes. Therefore, if you have a lot of unknowns, rent, look at partnerships, or get something cheap to feel your way into it. All you are trying to do is prevent over buying.
4. Put aside what you think the monthly spend will be. It can be used for renting or other aviation habits. Feel the financial pain first, and determine that is worth it. More people sell planes because the costs and budgets outran reality.
Last point, the whole step up in planes aspect, that was a concept created by salesman to make more money.
Tim