Getting to a point where I have set myself up financially and can bring myself to be frivolous and buy my F car. When I graduated from college the 360 was the current v8 convertible and I set my mind to getting one as my reward after the retirement was funded, mortgage was paid, and kids college funds are topped up. I suspect 1-2 bonus seasons, with one right around the corner, from now will be the time that happens. I kind of want a 458 (488 would be too frivolous in my book, because of the depreciation hit I'm sure to take during ownership) so I have been planning for that. But then I thought it might be cool instead to do the following: Get a 360 stick and drive it for a year Trade it + a little to get a F430 and drive it for a year Trade it + a little to get a 458 and drive it for a year Trade it + a little to get a 488 and drive it for a while The downside is the transaction cost I'm paying the dealer (or whomever) each time, but the upside is I get to experience the journey over time, I get to start with the car that was my motivation this whole time, I get to experience the "lasts" of the stick shift and the naturally aspirated engine, not to mention the lower up front cost to get the ball rolling, and move into a 488 at just about the time the depreciation should be mostly over with... What do you guys think? I'm wondering if I'll regret it because I'll be dealing with relatively older cars with potential to cost a lot in repairs on top of the transaction costs I'll incur. Still.... feels like it would be cool. haha.