Just to clarify, I definitely haven't already made this decision or anything yet - otherwise I wouldn't be on here. It's more of an idea I've had kicking around and something that would be done in lieu of vacations and other entertainment expenses.
I'm a big car fan myself, and I usually disagree with the general consensus on this board that everyone should drive a lightly used Accord for 20 years. I get your thought process, but I just think it's not a very smart financial decision. I appreciate that. A lot of people don't seem to understand the idea of cars as a passion and primary source of entertainment, and it gets annoying seeing how often any idea other than buying a soulless Honda and driving it up to 300,000 miles gets ridiculed.
How stable is your job? Pretty stable, and I've been there for a good period of time.
How old are you? 26. Retiring is a long way down the road.
You could be looking at a 5 year stretch where stocks are dirt cheap, and you miss out on a great opportunity to buy. Certainly something I've thought about. It's something I've been meaning to get into, but it seems the barrier of entry is quite high. I mean you can dump all your money in the S&P 500 and pray 2008 doesn't happen again, but it seems like making really informed investing decisions means tons and tons or research and reading, all of which has proven rather overwhelming when I've tried to get into it. I tend not to do much of anything unless I really understand it (let's call it half analysis paralysis and half being cautious), and I've never felt like stock investing is something I understand.
I still stand by my recommendation of a Cayman. I really wanted to love the Cayman, but I just couldn't get into it enough. Handling is definitely great, but the power downgrade from my current car (BMW E92 @ ~400hp) was too noticeable. Refinement and interior quality felt like a bit of a downgrade too. The E92 kind of spoiled me in that it's hard to find anything that feels like a worthwhile upgrade. At the same time, it's depreciated to the point where I don't want to hold onto it much longer and need to throw yet another $3,000 to $5,000 into it to do maintenance that isn't going to be reflected much/at all in its value, so I want to get rid of it before then. First world problems, I know.