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A leaking transmission does not necessitate a rebuild. You need to replace a gasket and maybe a seal or two, that's not the end of the world. It's actually not that hard on a 240 and shouldn't cost any huge amount. I don't see a rear seal and pan gasket replacement running more than $100. Front seal may be a bit more, but still nowhere near $1500 territory. Actual parts to do this are in the $30 - $40 range.
A taillight is not a problem. You can find used ones online for $20 or so and it takes five minutes to replace.
Not sure what you mean by "full horn assembly", but the actual horns are cheap and easy to replace, steering wheel pads less cheap, but still very easy. Still not a problem.
The airbox can also be easily replaced, but I have a hard time picturing how you would wind up with a trashed one barring an accident. Perhaps you need an airbox thermostat? They are $7 or so. 20 minutes to put in.
As far as the engine goes, why did it overheat? If it ran out of coolant, there is a leak needing to be fixed and maybe a new thermostat. Still not the end of the world.
Getting all the problems fixed in one go might add up to the price of a used car. The difference is, another used car will bring a different set of problems needing to be fixed. I go through used cars a lot, I like to tinker. The 240 in my experience has been the second cheapest car in terms of repairs after the pre-1994 Astro van.
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