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Without fail..
(i.redd.it)
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I still have Windows dual booted because I just can't figure these things out. Literally just now spent an hour trying to get Topaz Gigapixel working in Bottles and it just crashes, freezes, or sometimes doesn't launch. Installed vcredist dependencies only to have vague messages of "Failed to Install" Even tried ditching Bottles and just going through Steam and it failed there too. It's better than it was 10 years ago, but I'll have to keep a dual boot.
These days with how good KVM is, running Windows in a VM is a pretty good option.
Not that I'm against dual booting, but depending on how many programmes you're actually needing to boot into Windows for it can be a more convenient option.
On the other point, if you're struggling to get things working in Wine/Bottles/etc. when the internet tells you they should work, you could try looking into CrossOver by Codeweavers. It's a paid-for product from the company that does most of the development on Wine and Proton. Not everything can and will work in Wine/etc., but CrossOver has a free trial so it can't hurt to give it a go.
I'd be open to a VM, but in the case of Gigapixel it requires access to the GPU, which would disconnect it from the primary, my primary display. Thanks for the heads up on crossover, I'll look into it