Business-wise probably 15 times. I lost a lot of business in the first decade of my company, because there were (note the past tense) a lot of competitors and (sadly) "partners" that would attack us and/or use unscrupulous (I suspect some illegal as well) business practices.
I nearly lost my business twice. Instead of "turning to the dark side" / "if you can't beat 'em, join em," each time I concentrated on building relationships with my "good" customers and partners.
Nearly 20 years later, every single one of those unscrupulous actors are gone. Either bankrupt, fired, and in one case "rage quit." I'm still here, and although officially the companies that partnered with the bad guys don't admit it, off the record senior executives have told me they would have rather have worked with us back then, but they were under pressure internally.
Again I state that I understand explicitly the huge difference between bankruptcy and death.
That being said I also understand Faust and making a deal with the devil NEVER works out well.
Your argument that "Hitler was a montster, to put it mildly, but not a direct threat for Finland" is specious. Germany had concentration camps already in 1933.
By 1939 the Nazis had already annexed the Sudetenland Jews were stripped of rights and property and shipped off to concentration camps. Not only Jews were shipped off to the camps. Anyone seen to be a threat to concentration camps. This is personal for me as my wife's grandfather, a local cop in Czechia, was sent to Buchenwald. He was a Christian Slav.
By 1939 the Nazis had also already annexed Austria. Just like in the Sudetenland, Jews were stripped of property and rights and they and anyone seen as a threat were first identified and then rounded up and sent to concentration camps. Mauthausen, the largest slave labor camp in Austria, already opened in March 1938.
https://www.mauthausen-memorial.org/de/Wissen/Das-Konzentrationslager-Mauthausen-1938-1945
Of course in 1939 news did not travel at speeds close to what it does today, but it was already WELL known in both Europe and the US what the Nazis were doing to ther own countrymen, let alone those of the countries they "partnered" with.
To side with the Nazis to fight the Soviets, the Finns had to make (IMO) a conscious choice to accept the deaths of their own citizens at their own hands through a partnership with the Nazis, even if they defeated the Soviets (which they didn't, by the way).
