You are going to need correct agreed value insurance on it, not geico, etc., which means a locked garage, probably at least 25 years old. You're almost there, plus you'll need a relatively clean license. Garage is the big thing. Gotta keep it nice so it does not depreciate like the 5th gen you got that dropped 20% in value in the 1st 3 miles. You are also going to need a pretty good credit score in this market - maybe 680+.
Here....
http://www.hagerty.com/assets/PDF/FinancingOptions.pdf
http://www.woodsidecredit.com/FAQ.asp
» Does it matter where I buy the car?
No. You can buy your car from a dealer or a private party as long as the car is eligible for our program.
http://www.motorcarsfinancial.com/dsp_faq.cfm
I won't bore you with the whole how to spend you're money, save for a house, etc as I don't know your deal. That's on you. But if you are making payments on that 5th gen maybe 2 car payments is not the best idea. Cars are illiquid assets, meaning they take longer to turn into cash, compared to something highly liquid like a stock that generally takes seconds.