Do what makes you happy, you can't put a price on happiness.
People can go their whole lives with all the money in the world but if you don't use it or live life to it's fullest you'll just miss out.
If your dream car is a Supra. Get a Supra. Then you can tell everyone you are living the dream.
I 100% agree with you, you work to live not live to work! You cannot take that money with you when you die and you never want to look back on your life and say "I wish I did that". Do it! If it turns out to be a mistake, well it does not matter as long as you learn from it. There is a fine line between hoarding for retirement and saving for it and enjoying "the now". Balancing the two is the hard part. Like posted above make sure you have security money(not 1k, but about 6 months of living expenses or for something catastrophic). The last thing you want to happen is to buy one then have something horrible happen. Quick example- I just bought mine over a month ago and blew a piston ring, if you can't do you own labor it adds up FAST. I decided to do a full 6sp swap and build the block/heads/triple disk clutch/suspension/etc.. so far I'm at almost 30K in parts an labor. But, not a cent has to go on my CC I can pay cash and still not worry. But that is my scenerio, I've been fortunate to be able to do that but it took hard work and alot of school. Just be smart about it and don't be a llittle kid in a candy store and blow your whole LOAD at once (Pun intended, LMAO) becasue if something does go wrong you don't want to look at the car every day waiting to get the money to fix it. Just my 2 cents from my experiences, but don't get me wrong I do own my drem car since high school, minus the new GTR, well R34 then, sometime soon though- supra and GTR in my garage, MMMMMM- I'll set up a cott in my garage and sleep in it, LOL, JK! Good luck!