Ongoing car advice

[RobertInOntario]

Over the years, I've received good car advice on this forum and have posted car questions a couple times. Here's an update on our ongoing car "saga":

My wife & I have two "aging" cars with fairly high mileage. We have a 2003 Subaru Legacy (our family car) and a 1998 Honda Civic (which I often use). Here are their descriptions:

• 2003 Subaru Legacy -- has about 200,000 km (about 120,000 miles) on it
-- body in good shape, very little rust but lots of scratches
-- has had several costly repairs during 2009-2011 -- (new transmission, has had the clutch replaced twice) and there may be other things to go on it too such as a possible steering problem that my local garage has been monitoring for us.
-- MAJOR UPCOMING EXPENSE: Yesterday, I just learned that its cylinders are leaking oil. This is a major repair that could cost over $2,000.
-- it may also be in need of a major tune-up soon as it has been running roughly (misfiring) after starting it up, when it's very cold.

• 1998 Honda Civic
-- has 220,000 km (about 140,000 miles) on it
-- has had very few major repairs, mostly minor / regular maintenance
-- body is rusting more & more, especially bad around rear fenders. It has many scratches and/or paint problems (thanks to living in a big city)
-- its parking brake is broken -- which is a messy repair & could cost $500+
-- otherwise it runs very well & smoothly!

So, which car should we replace? as both are increasingly wearing out. I'm tempted to have the Subaru repaired as long as the rest of it will keep going and replace the rusting Honda, but it's a gamble either way. We also might have an opportunity to buy a 10-year-old car with low mileage (for a low price) from one of my wife's work colleagues, so that could be good.

At any rate, we need to do something soon & we certainly can't afford to replace both cars.

Thanks in advance for any thoughts and feedback!