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You don't say whether the 940 is a turbo or not, but I'm guessing it's just the NA GL model. If so, I would keep the 240.
I believe both cars have the B230F engine. If I were the one getting a new car, improving performance would be my number one concern. The 940 is a few hundred (maybe just 100) pounds heavier than the 240 but with the same engine. Thus, in my eyes, a 240 is the better car.
Even if it is a 940 turbo, I'd still be torn about selling the 240. I'm familiar with my car and have begun doing what I can to make it better, and so I'd really be hesitant to spend cash to get what is presumably a "baseline" model (no ipd sways, no custom "upgrades," etc.). The 940T does have an extra 40hp, so only a driving test could tell me if losing the old car and spending a couple grand would be worth it. Probably, though, if I were the one in your situation, I'd wait for an early 960 (200hp!).
Plus, you've already got a 940. For some reason suggesting that you keep things diverse seems like good advice.
Lastly, if it were an option, I'd say buy the 940 and keep the 240. I got my mom's 240 when I began driving, probably six months after I got my daytime license, and she got a brand-new Volvo. You don't seem like the type to go for the S40 that she wanted, but the 940 would be the equivalent upgrade for your situation. I don't know if that's a possibility, but the 240 is definitely a great car for giving to beginning drivers. It's decently hard to do really stupid stuff in it, and if your son is in an accident, you'll know he's in one of the safest cars on the road (he'll probably be able to drive it home!).
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'89 244 GL--25/22 ipd sways, Volvo truck amber turn signal lenses
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