I have a 2003 outback limited with 156k was told I need a new water pump, replace head gaskets, need new oil pan and oil pump leaking also new drive belts transmission pan leaking too. Cost $3400,

Depends... I would probably use the $3,500 for a down payment on a new or late model car, but, that's me..... It's all about what you want to spend. Least expensive option is to just fix the car provided the transmission is in good condition, otherwise, get rid of it. YES, I understand it seems expensive, but, $3,500 is close to the sales tax on most new cars , you'll pay for for insurance, depreciation in the first couple of years, financing, registration fees, it all adds up. AND, even if you go only another 44,000 miles to 200,000 , the cost for this will only less than 10 cents per mile. SAFETY features is the only way to justify a newer car...

Even though it's the value of car, it's all about the service you will get in return... Resale value is NOT important unless you intend to sell the car. http://www.nadaguides.com/Cars/2003/Subaru/Legacy-4- Cyl/Wagon-5D-Outback-Limited-AWD/Values