2012 c250 sedan

Palladium Silver/MB Tex
536 Sirius sat radio
S32 COMAND Single Disc Package
MSRP: 37,785.00

I have trade in value of 8k in my current OWNED car
With additional 1k down i get the following.....

Gross Capitalized cost: 36399 + 1095 acquisition fee + maintenance 1119 = $38613
Adjusted Capialized cost: $29573
Residual Value: $24,289
33 months 15k/year
306/month

I went to the dealer set on purchasing an 09 c300 with 26k miles. they were going to do 25k out the door with 8k on my trade in + 5k cash down, payments were going to be ~200/month. The way i look at it, in 3 years, i will easily lose that 8k from the honda and could only hope that my 5k was still there, in 2015 how much can an 09 c300 with ~70k miles possibly be worth??. then i realized if i lease a brand new one, yea i pay more monthly, but its a brand new car, and my 5k stays in the bank. when the lease is over, I've lost my trade in value, but that would have been lost no matter which car i was driving.

any feedback...