Wineskin is somewhat easier to setup than normal Wine (its a branch of it):
Also, in general, at least if games are already in its library, porting kit is a collection of Wine "recipes" (sets of libraries and settings to get specific games running), which is often the easiest way to install Win games:
http://portingkit.com/en/
Unfortunately, HoMM2 isn't included yet and seems to be a DOS game originally, so you would ideally have to set up Dosbox properly (or Boxer, a somewhat more convenient Mac version of it) to start the game file.
... or you run Dosbox inside Wine (which is a bit convoluted but quicker to setup). Since its an old game it should work fine without too much performance loss though.
Here are the steps for the Wineskin way:
• From this page download the Winery (a setup program for Wineskin Wrappers):
http://wineskin.urgesoftware.com/tiki-index.php?page=Downloads • Not sure if it includes an engine already when doing a fresh install, so just in case: In the little window that opens click the plus icon to get a list of available Wine engines (the "core" that does the translation of calls). For old games like this I guess any should work, just get the most recent one.
• Select create a blank wrapper; name it properly, click okay on the following pop ups
• Go to: your user folder/applications/wineskin/yourwrapper
• Normal double click won't work yet (as it doesn't have anything installed yet). Hold down the option key (alt) and double click the app. A config window should open up then. Alternatively, right click on the wrapper, select show package contents and in the new window double click wineskin.
• Select install new software, and in the Installer window that opens select "Choose setup executable", navigate to your Homm2 installer. Let it run, ignore the errors that pop up, that has been happening with GOG installers for a while, but the install should be fine. Click exit when its finished.
• In the new window that opens up (choose setup exe) select DOSBOX.exe, it should be among the drop down menu options.
• unfortunately thats not enough, as gog uses a link with instructions for DOSBOX to select a configuration file. You would have to tell DOSBOX the same thing
• right click on the wrapper you created (inside the Wineskin folder in your user folder). Go to drive c/GOG Games/Homm2 folder (dunno how its called).
You should find the config files for Dosbox inside this one. Copy the name of the file. usually similar to dosboxGAMENAME.conf.
• In the Wineskin main window select advanced options. You should see a window with all sorts of text fields and the path to DOSBOX.exe in the Windows EXE field (the top one).
We need the Exe Flags field now. Copy in:
-conf "..\dosboxGAMENAME.conf" -conf "..\dosboxGAMENAME_single.conf" -noconsole -c exit
• Replace GAMENAME with the name you saw and copied in the folder.
(Assuming that the configuration files are named similar to the game I used as reference here).
• Last thing:
Click Set screen options in the middle at the bottom. Deselect Auto Detect GPU (as its broken in the most recent OSX version).
Also setting the window to rootless and the Virtual Desktop to something like 800x600 up to 1024x768 worked better for me than going Fullscreen. Depends on the game.
• Either exit the wineskin config app now and try double clicking your created Homm2 wrapper (it should work now) or click Test Run inside the Config app (this shows a debug console after running to see if you are missing libraries for example)
If the screen stays black hit esc, command-q or in worst case scenarios command-alt-esc. But all of those should bring you back to the desktop if Wine doesn't show anything. In this case messing around with the screen options might help. No definite answer for that.
But that should be enough to get it started. Sounds kinda complicated but it really just takes 15 minutes. For other games, using newer tech its sometimes less straight forward (or way easier when its available in porting kit).