I think I considered Elementary at one point but was worried about the stability of the distro at the time (aka, if it would be kept up to date).

Yeah, I have tried the linux alternative to most of these programs but they just are not up to the same level last I tried them.

For office my Mom has hundreds of macros and settings setup exactly how she needs them, is it possible to transfer all of those settings and macros to Liberoffice? I have not looked if it supports office macros. I have wanted to switch her from office 2003 (anything newer is “too smart for it’s own good” and annoys her) for some time.

Adobe, DXO, Vegas and solidworks do not have competitors worth talking about on linux that I have seen (no, Gimp does not count for my uses).

Another issue are the little programs like an advanced file finder my Mom uses that allows her to rename files within the program itself like explorer, she refuses to use anything that does not allow that.