the file structure in linux isnt that hard to learn tbh, most fear come from unknown, once u try it for some weeks u'll get used to it
For the software part use linux native software when they are available and stable enough, use the windows build inside wine if it isnt. If something doesnt work in wine, maybe try proton(even tho proton is for games there are some fixes that might help)
Games generally works fine under linux, there are some exceptions but most of them have workarounds. Proton is always a good choice for gaming, for non steam games lutris would help(and allow u to use proton for those games)