I have 2 business machines here with notices for Windows 10 upgrade. I'm also skeptical about doing this as I will be crippled if the upgrade hoses my computers. Also, I'm still running Office 2007. Is it even compatible with Windows 10?
I really understand your concern Gene and this is very much a common fear. You're so dependent on the systems and in fact if you get downtime your business will actually suffer immediately. I've just been to a seminar with some of the Microsoft windows product managers and from their point of view the number one key factor of win10 is to secure the upgrade process, no matter what you have, no matter which devices you have.
From what I have tested win10, i had absolutely zero issues with anything, any Microsoft product, any third party product, any drivers, and that was with the technical preview version one.
From my experience, I never do upgrades of windows, always clean installs, and always use the Microsoft version of windows, don't even touch the OEM versions that comes with a bunch of bloatware. Not 100% sure then how to retrofit the Office 2007 licenses, but I believe a clean install of office 2007 and reactivation with the codes you have should work, this should be possible to check beforehand with Microsoft, at least it's what I think.
It's a lot of work to do a clean install and to retrofit all you do have but in my opinion it's worth it, experience show that the upgrade bring with you dll's, assemblies and other legacy stuff that you don't need and that's gonna slow you down and possibly haunt you in the end.
The win32 API, from which also office 2007 relies, should be 100% backward compatible, which means all programs that use the supported functions in the win32 api should be safe, which means Microsoft programs should be safe. I can't guarantee but it's what I think.
There are ways to secure yourself so you know for sure......
Before doing a jump you can test on a separate disk, even install onto an external USB disk, but if we really do have mission critical systems it's really preferable to test on another computer that doesn't disrupt your business. Even though an upgrade should not fail it will sometimes, so then you need to find ways to secure your steps.
You know where to find me if you have questions Gene
I'm working closer with Microsoft technology now than I ever did in my life
I believe the next major wave we will see in the computer world will be from Redmond!