The software will likely work, but keep in mind that you'll have to add VM startup time when you want to use the software. I have occasionally seen software behave strangely in a VM as well, so best to just try it.
Can you share the software you went to use? Maybe there's a good Linux alternative or someone knows how to get it working in wine.
Same.
I use Bortmatic to manage my repos and I pay a little bit to BorgBase for offsite backup of my important stuff.