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Does a program like Parallels handle font scaling with Windows better than BootCamp?

Retina screens with BootCamp make windows unusable.

Yes, it does. But be warned you will end up trapped in an upgrade cycle. It's common for major updates of OS X to break Parallels and then Parallels will release a major update to fix it but charge you for it. As long as you're prepared to buy a new version of Parallels every year you'll be fine.
 
Yes, it does. But be warned you will end up trapped in an upgrade cycle. It's common for major updates of OS X to break Parallels and then Parallels will release a major update to fix it but charge you for it. As long as you're prepared to buy a new version of Parallels every year you'll be fine.

Thanks for the warning, not sure if I like being held up by gunpoint to force me to upgrade!
 
IME it's usually every two years for Parallels. They grudgingly support the n-1 version for the current OS but not with all the bells whistles. I'm still on v10, but will likely have to upgrade if I want to continue running it on Sierra.

They're knocking v11 out at at a discount currently but it's a bad buy as v12 is in private beta. I'd suggest waiting until they offer v11 with a free upgrade to v12 which will likely be in a couple of months time.
 
But be warned you will end up trapped in an upgrade cycle.
In the macOS forum, people seem to be reporting no issues with Parallels and the beta, unlike prior times where the beta broke parallels.

Personally, I did not like the scaling that vmware provided compared to bootcamp, but i've not revisited that for a long time, and parallels may do a better job.
 
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