Is it bad to transfer old software and files from an old Mac to new Mac?

No it is not bad to transfer data from old Mac to new Mac. How else will you get your data? I never transfer apps, I reinstall them so that I am starting out fresh with my new computer. If you have old apps they may no longer be compatible with your new computer's operating system so just blindly transferring apps is not a good idea.

I think I addressed that in my post above. I always do a fresh install of apps. Old software sometimes in not compatible with the new operating system. To avoid any possible issues I install apps rather than transfer them. Do a little research with the developers of your apps to see what version will be compatible with your new operating system. Here is a start from Microsoft: Microsoft Office support for macOS 10.13 High Sierra - Office Support

One aspect is it depends upon how you do the transferring. If you migrate it should work for anything but if you are dragging from one drive to another you can leave behind components that were stored in places not so readily apparent to you. Some of these may regenerate and it doens't really matter, but others may leave behind critical components and you either need to dig through your hidden folders for cryptic names or you need to reinstall fresh.

I tend to use software until a new system completely breaks it. That said, I have some software that seems to work without issue but if I look at system logs I can see error messages being generated. I kind of take the 'if it works then okay' attitude to this because i do not always want to use a newer version of the software.

1. Only if you’re having trouble with the old computer.

2. See #1.

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It depends on whether they’re compatible with the new Mac’s OS. For example, Microsoft Office 2004 won’t run in anything newer than 10.6.8.

Click here and look them up.

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