is better to copy entire home folder to a external harddrive if you like to use option 2.
in the case that you forget something, do not forget that wine folder is hiden folder you most on home folder on top menu select view and then select show hiden folders. this .wine folder is the only folder from hiden folders that you need to copy to external harddrive. when the new O.S is installed you most again select again show hiden folders and copy this folder from external harddrive to the MS home folder. inside this folder are the all vst you got with MS.