ubuntu 16.04 Vs 18.04

I am wondering if I can boot ubuntu 18.04 on a ssd and use files from a 2TB hdd in ubuntu 16.04. or must I use a dual boot which would defeat my purpose.? The reason I ask is that I have a few programs that only open in WINE, this is all good on 16.04 but I am unable to install it on 18.04. Any help would be appreciated, with directions on how to do it. Regards, Rod…..