09 Legacy Needs Head Gasket + Timing Belt - Time to Upgrade?

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I just hit 100k. Dealer says Head Gaskets are leaking. To do HG repair with Timing Belt maintenance is quoted at $3500-$4000 (if any heads warped, so I'm estimating conservatively).

The only other major maintenance that I've done is a clutch replacement at 60k for $1600 so I'm concerned about that happening again.

So I'm looking now at $4k in work on a 2009 Legacy 2.5i base model with 100k. Is it worth putting that cash toward an upgrade at this point? Any other major maintenance on the horizon?
 
We just had to make a similar decision. My wife’s ‘05 Outback XT had just had an expensive fuel injector repair, was having automatic transmission issues and a suspension problem. Several other pricey repairs had also been done earlier this year. The car only had 130,000 miles. But had we put the money, which we could afford, into fixing all the issues we still would have had an almost 15 year old car that my wife uses to commute to work every day in heavy traffic. And we would have just been waiting for the next shoe to drop. We traded and purchased a 2020 Outback. It really comes down to what’s affordable and what your comfort level will be after fixing all that you’re looking at.
 

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