1995 Jetta - repair or retire?

My power steering went out the other day. Took it to the dealer and they said it'll cost $1500 to fix -- the big items: replacing the power steering rack and the power steering pump. I'm sure I can get this done cheaper elsewhere...but I'm wondering if it's worth it. I've had the car since 1994 (coming up on 8 years), the A/C hasn't been working for a year now, and the paint on the roof and trunk has oxidized. It has 88,000 miles, so I'll probably hit 100K in about a year (i.e., no more powertrain warranty).
Should I suck it up and pay to fix it? I LOVE this car and got it brand new. But I'm thinking that with all the other expected repairs, it might not be worth it in the long run. Has anyone ever had trouble letting go of their VW?
It's going to be a heart-wrenching experience if I have to do it!
Should I suck it up and pay to fix it? I LOVE this car and got it brand new. But I'm thinking that with all the other expected repairs, it might not be worth it in the long run. Has anyone ever had trouble letting go of their VW?

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Comments
Before you go much further, I suggest you get an estimate from an independent shop. It may be significantly lower.
But, if indeed both items are toast, I agree that you should shop an independent shop.
If you try to sell this car with bad a/c, bad rack, bad pump and bad paint, you aren't going to get very much for it. So unless you are ready to bail out and buy another new car, you'd better at least patch it up before you sell it. Fix the steering, even with some used parts if you have to, get the paint buffed out, and then sell it. But as is, you'd be lucky to get $2,000 for it and even that won't be easy.
Patched up and cleaned up, you might get $4,500. So would be spend say $1,000 to make $2,500? Sure, but no sense spending $2,200 to make $2,500, I agree.
I will get another estimate and attempt to at least partially fix it. Not sure about whether the rack and pump died simultaneously... You're about right on the value. The VW dealer "appraised" it at $2500. Maybe I should just work with them and do a trade-in.
Thanks all!
What kind of car did you end up getting??? I'm very curious. I test drove an Acura RSX, Mazda Miata, and Jetta GSL 1.8T over the weekend. All were great, but the Acura was by far the most fun to drive (in my opinion). Very cool interior too.
If it were me, I'd trade in at a VW dealer for a USED car. Let someone else take the hit on depreciation.
note this... your dealer is NOT going to put this car on his lot. he is going to wholesale it through auction, and it will end up on an independent corner used car lot. those guys will do what they can on the paint, nothing on the cruise, and maybe hink with the a/c, maybe not. what they're going to look for is whether the car is burning oil, a scummy pit inside, if the tires are worn evenly, if it runs well or has flaws.
it it does that... drives, turns, and brakes, the tunes play, and it doesn't shed parts all over the road... they'll give you something. probably lower end of the "good" condition scale, "and we're doing it because it's the end of the month and we're a couple cars short of making quota for all the stock we want going into winter." you know the score.
the a/c probably will cost $200 to fix with junkyard pulls if the corner lot tries it, and they'll use colored wax if they have to over the iffy paint. to "fix it right" before you trade costs a lot more, potentially most of what you will get in trade.
that's my two cents... probably better to get it running and safe, and let the rest of the cash assist in your down payment, etc.
now, if you were to keep the car, it might be worth fixing for your comfort and prestige, but not as an investment. as the old saw goes, it's always cheaper to repair than buy a new car. as long as it can stil be described as a "car", not a "planter" or "security roadblock."