Windows vs. OS X have quite different philosophies in font rendering:
> https://blog.codinghorror.com/font-rendering-respecting-the-...
"Apple generally believes that the goal of the algorithm should be to preserve the design of the typeface as much as possible, even at the cost of a little bit of blurriness.
Microsoft generally believes that the shape of each letter should be hammered into pixel boundaries to prevent blur and improve readability, even at the cost of not being true to the typeface."
Also under Windows font hintings and other subtile details of the font format have much more importance on a good-looking font display than in the font rendering algorithm than under OS X.
Source:
> https://www.smashingmagazine.com/2012/04/a-closer-look-at-fo...
(This article is from 2012; I don't know whether it is still up-to-date):
"On Mac OS and iOS, we hardly have any control over the rendering, which is acceptable (since it’s generally very reliable). [...] On Windows, hinting matters—especially for TrueType-based fonts (the only Web fonts Internet Explorer 6–8 will accept). Apart from that, one significant control we have over the rendering is the choice between TrueType and PostScript. Except for very well-hinted fonts in smaller sizes, the latter is equal or superior in rendering, and easier to produce. Even though DirectWrite is making Windows rendering more pleasant, it will not remove the necessity to provide well-hinted fonts."
That doesn't really solve your other issues though. Personally I use lastpass which works fine in Linux but I haven't used 1password enough to be able to say whether it's a valid comparison or not. Lightroom might work under Wine or in a VM if you don't use it so often that you really need it to be native.