I switched from Cygwin to Msys2 a year or two ago and it's been very good. The pacman-based package management is very good. The only thing to watch out for is that there are actually 2 gcc suites and if you want to build automake projects (like many open source projects), you'll want to be using the Mingw gcc and NOT the Msys gcc. ConEmu is a great terminal program to use in conjunction with Msys2
I also recommend opinionated Emacs distros. I used to use Prelude but I've been using Spacemacs (in Emacs mode) for quite a while, now. I like Spacemacs because your loaded packages are explicitly in your .spacemacs file and it's easy to reconstruct which packages you have loaded from that.