I'd like to know if it is legal to install the msttcorefonts package and also if installing Windows software using Wine is also legal? I currently live in Brazil and I don't know what specific rules apply over here, but would appreciate any feedback on this matter. Thanks in advance!
In short: It's not a case of copyright law because Microsoft allows the redistribution of the font installers and it allows users to install the fonts (regardless of OS).
It does not allow for redistribution of the TTF font files on their own, so, for example, it would not allow for a distribution like Ubuntu to include them by default.
Sidebar: The newer (Vista-era) fonts like Consolas, Segoe, Cambria, Candara have explicit "only for Windows" junk in their licenses, but these fonts aren't included in
Wine is less black and white.
If you need a bullet-proof legal way to run a Windows application from within Ubuntu, virtualisation is probably the key. A real licensed copy of Windows running will do almost anything you want it to (with a performance hit).
I am not a lawyer, but generally speaking packages that are included in the official Ubuntu repositories are not encumbered by any copyright or patent restrictions that would make it a tort or crime to install. A number of useful packages are excluded from the official software sources because it would be unlawful for some users in some places to install them, due to such concerns. One example of such a package is