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I had an 87 535is, was in our family since new. We put 200k miles on it, I did around 150K of them (from 50K to 200K).
I also did all of the work on it for my 150K miles.
It was a very good car. It wouldn't have been if I wasn't a DIY'er, though.
Plenty of little (but necessary) repairs and diagnostics over the years, most were not major and were very little work and money for me. But if I had to take it to a shop for every one of them, it would have been ridiculous.
Oddly, HVAC was never an issue. It worked perfectly with no repairs the entire 200K miles.
As much as I love the E28, I wouldn't recommend it for you at this point. It's just too old of a car. And the E28 is more complex than the earlier, smaller BMWs like E21 and E30. For example, there's a ton of soft parts in the E28 suspension, when they wear they need to be replaced or you get shimmies, etc.
Like with most 30 year old cars, they are still totally fine for enthusiasts who want to have some fun, tinker, etc.
But when the purpose is for "a commuting car for about 10 miles/day, in traffic, that is reliable and looks respectable, with working AC" I'd not recommend it.
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