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Take pen and paper and add up you your monthly payment over a year. If you do this then you never have to worry about loosing flexi, BUT if your always going to be in the business then why worry about it. Design in flexi and photoshop or on the corel platform. This is why i always try to inform people about using this software for a basic rip ONLY. Well, while we still have the option anyway. That may or may not be the case for you though, so definitely price it out, but just be mindful how you price it out and project it over sufficient time.
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I do plan on being in my industry for longer then 7 yrs (fingers crossed). When I was pricing out what I needed from Adobe when they offered both, in 7 yrs, I would have paid more for subscription then upgrading every new generation. Most people only think of it as per month with no memory or projection of the other months. Bare in mind, that when you calculate C/B, subscription is not only the current month cost, but the previous month's (or months) cost as well over the life time you plan on using the software. Typically in general terms (not all the time though), subscriptions almost always cost you more then buying outright, it just depends on how far out you look. That's going to be the biggest thing in determining how well this workflow with be. Not the same thing that I was running before with only Win 7. To be honest, my setup running 2 OSs and the programs that I need is actually faster then when Win 7 and the same programs were installed directly onto the machine, but I'm using different hardware. The biggest thing that you have to be aware of is the resource needs of both OSs and the program(s) you are planning on running, especially concurrently. I use virtualization in my work flow as well, except I do Linux host to Win 7 guest using VirtualBox. I can't speak to your exact situation (as far as running RIPs etc), however, I think I can help with the situation in general terms.