Dude: You're killin' me. Some thoughts: First, I assume from the $ and just working that you are very young. Okay, no problem...you've been given some good advice here already. A 3 series BMW from years ago is not going to be a big insurance drain anymore than oodles of other cars. I suspect you would have loads of fun. However, you definitely need to consider annual cost to maintain and repair any of the used cars you consider and I am LOL about leasing a 1 series...c'mon. An older BMW is the poster child for expensive repairs and most young budgets cannot handle them because they are maxed out already on the purchase/loan payment, gas, insurance, babes, etc. Just ask the service men at the $100/hr. dealership if they discount for older cars...that sound you'll hear is laughter. Just today, I posted an inquiry here about selling my 2001 740i DINAN modified Sport model which is exactly the kind of combination you should look for but in a more age/intent appropriate model. That car is going to be a huge value for someone under $20K. As another replied, you could find a nicely modified car rather than do it at full cost and you won't pay the full boat. That buyer of my car and similar others, though, should be allowing four figures to repair it each year and you just don't sound like that kinda guy. I'm also laughing out loud because you said you don't think a powerful RWD car is smart in the snow...THEN WHAT ARE YOU LOOKING AT THESE POWERFUL RWD BMWs FOR!?!?!? And, as also noted by others, Supras and RX7 are precisely that, as well! I replied to you in part because I owned three Supras and LOVED them. And, let's just say I was quite "successful" in them. But, once you get up in miles you are looking at expensive repairs (read Timing, cam towers, yada yada) just like a BMW. I am also laughing because over the years I'd visit the BMW dealership and not even make it to a test drive because I was dissappointed that they did not have a "sports" car like my Supras...to which the sales people would take some high-n-mighty position as though the 3 series was actually a superior performer and I would laugh at them. If only I knew then what I know now about handling and performance I'd have bought a Bimmer long ago because they were spot-on and I was to stupid to see it until twelve years later! There is no Japanese car like that that compares. Young Sir, you need to insulate yourself from a big error by getting something new enough to take advantage of more recent reliability and perhaps, as a byproduct, lower miles, repairs, etc. Without knowing pricing, I'd say a three or four year old Mini with some cool mods and a long warranty is your best bet. A warranty would allow you to overpay by a couple thou and be happy about it. All the Japanese cars you mentioned lose their class and cool at the age you've suggested and the 3 series or Mini from a few years ago would have that along with a ride you'll never regret. If you go older on the 3 series, my only advice is they are a dime a dozen and you should drive a hard bargain for $6-8K on something worth $12 retail but just pay dealer trade value and expect to shell out more later. Good luck. P.S., if you're older, you should buy my 7 series and you'll never look back...but you gotta be around late 20s, at least. It's funny about the guy who likes American Muscle (as I do)...with my DINAN mods, the cars my 7 series sounds most like are 70s muscle cars...OOOOoooh the rumble!