I think I may understand the difficulty you are having, as I had similar problems until I learned the 'secret' to making WINE work well consistently. In my case I had to UNINSTALL wine and install WINETRICKS. Winetricks installs a full package of MS fonts including "mono", as well as other support items. With the fonts in place, programs requiring such fonts will install so smoothly, you might imagine you are installing Office on a Windows computer.
Whenever advising others regarding windows software under Ubuntu my advice is to install Winetricks first then PlayOnLinux second. After installing each in sequence, then open Wine (which is installed by Winetricks) as Wine must be opened once to auto-configure and update itself further, before trying to install software.
Finally, if I recall correctly it was PlayOnLinux which contains installation help for MS-office, although both Winetricks and PlayOnLinux both contain installation help.
About all I would add is that although there are certain specific features of MS-Word not substituted adequately by LibreOffice Writer, such as "markup", I have been able to demonstrate that for most people without that requirement Writer is actually preferable has features omitted from Word including some add-ons MS has the audacity to require their customers to pay extra for.