Hi, just joined, and wanted to say to any Linux users, that HL works perfectly on Wine 3.0 (last stable version as of June 16th 2018) , making sure you have installed anything you might need to run Steam.
I usually manage several Wine versions through PlayOnLinux, but after installing HL in the same 3.0 virtual drive I have my Steam (for those few games I own that aren't for Linux), the program works awesomely well (been using it for hours with no glitches or crashes).
Anyway, just wanted to share that. Sorry if I made any grammatical mistakes, English isn't my main language.