Type winecfg in terminal and go to the graphics tab and tick the emulate virtual desktop option there. This should solve the misplaced content problem.
Also, using winetricks directly installs corefonts in the default wine prefix that is at ~/.wine (~/ means your home directory. ".wine" is a hidden folder in your home directory).
A wine prefix is like an isolated windows installation. You can create as many wineprefix as you may want. This is used to isolate programs with problematic dependencies like dotNet4 and directx9 since most programs don't need these. For the programs that do need these you should use a seperate wineprefix.
Here is how to install corefonts in playonlinux and play big brother.
1 Open playonlinux
2 Click on the big configure button.
3 Click on the new button on the bottom left.
4 Click next , select 32bit installation , click next , select whatever wine version you want, click next , name the virtual drive or wineprefix (I named it bigbrother), wait while the virtual drive is created and it's done.
5 Now click on bigbrother in the left sidebar .
6 Click on the wine tab and click on configure wine.
7 Go to the graphics tab and tick the emulate virtual desktop option there and close the window.
8 Now go to install components tab and select Microsoft Core Fonts there and click install.
9 After that's done , click on the Miscellaneous tab and click on run a .exe file in this virtual drive button. Find the big brother exe and run it using the file picker dialog.