I think the closest to obscure software I’ve had to use Lutris to get working is some crossword puzzle maker that only has a windows version. One day it just stopped working using just wine, so I switched to Lutris just to make it work.

Edit:

The software was last updated July 27 2022. It can generate HTML and interactive HTML when you’re finished, which is why I got it. That, and it was the first open source one I found for windows. Only got it on my laptop because I knew it had features I care about and would most likely run fine through wine.

It’s Crossword Designer.

If it’s official moves only, metronome because the randomness would be perfect.

If we’re including custom moves people have created, I would absolutely do my better version of metronome. It’s better because it contains only 1 turn attacking moves in its move pool. Every single one of them, so I’d have just as likely of a chance of being hit by ember as I would oblivion wing or sludge bomb or rock slide.