Wine works really well on popular games. But when I want to run a more obscure program I have spotty luck.

On a few of occasions I was able to get a few programs to run via Wine, but after an OS wipe I was unable to get them to work again. In those circumstances I know the programs CAN work, & I realize how terrible I am at troubleshooting Wine problems. Internet searches turn up very little advice for how to go about troubleshooting.

Do any of you have any procedures, rules of thumb, advice etc for troubleshooting Wine issues?