The mid-century modern windows are not in great shape and would need to be fixed.
Original single-pane wood windows would be a hard sell for you. No matter how nice the windows look, buyers will still look at them as a detriment. Many buyers will mentally figure replacement costs into their offering price on your house.
Keeping original windows (even ones that aren’t especially energy-wise) can make sense if you have an older, more historically-significant house. Some buyers will value these. But not a lot of people place value on 1950s windows, despite the current interest in Mid-Century Everything. Windows seem to have escaped the nostalgia for Mid-Century things.
Unless you’re had window companies raise red flags, I don’t see where any of them would be concerned about the asbestos siding. Replacement windows work with the available space. The installers don’t open up that space (which would mean cutting into that asbestos siding). Sometimes, they will shrink down the space a bit, but never open it up. It’s carpentry, and these installers don’t do carpentry.
If you’re in the kind of neighborhood where vinyl windows aren’t out of place, I recommend going this route–and having someone else install them, cheaply.
Replacing them yourself will get old very quickly. First, you need to find a place that will sell you replacement windows, not new-construction windows. New-construction windows are the type you see on the racks at Lowe’s and The Home Depot. They have “fans” that allow you to nail them into the house siding. Replacement windows don’t have those fans.
But that’s a minor issue, compared to how tedious it gets when you try to replace 25-30 windows. The first couple of windows are kind of fun. The next few are nice, because you know what you’re doing and you feel confident. After that, it’s assembly line work.