I am assuming the answer is impossible but I was wondering if it is possible for estimate 1.991 to be put on a new computer.
This depends. Sometimes it's possible. One of the few goods things about the legacy bloat of Windows is the better chance of older software working on newer OS versions. Not always the case, but it is possible. It may install, but your workflow may trigger a bug, so could be something like that. I wouldn't expect any support for it however.
The main problem I have with the subscription version is that we were sent instructions to migrate out own data in such a fashion that I have zero confidence that the new cloud based system will even work with our old data.
Again possible, but I would have more confidence with sticking with the same vendor then trying to import it in for another vendor. I would however, make sure you have backups of your files before migrating (if you do go that route), that way if something does happen, still have a copy of them.
Have a few options, some are better then others, some just depend on how much time you have to devote to this.
Depending on if you have the serial number for the OS and that particular OS is supported by your virtualizing software of choice, could virtualize the older OS to run your quoting software. Use "shared folders" so that way your info isn't stuck in the VM etc. You would want to make sure to spec out your new(er) computer can handle virtualization. A lot of people think that it takes too much of a hit performance wise and this really comes from not correctly matching the specs of the computer to handle essentially running two computers at once when the VM is running. I've run VMs within VMs and I've edited HD videos in VMs with almost spot on native performance, so it really does depend on how you spec it out.
Another option is emulating the older OS for the software. A lot of people think of VM and emulating as the same thing, there is one key difference and that key difference is why emulation does have a performance hit no matter what hardware you have. For an estimating program, probably not that big of a deal, but for major production work, it's no bueno. I would only use this option if a VM software that you are looking at doesn't support the OS that you are needing to use.
Could always VM for legacy needs and create your own solution for future orders (maybe use the VM until you have your own solution completed). Most estimating programs are essentially spreadsheets under the hood. Just with a nice flashy GUI that people see on the front end. It might take time to create your own solution, but it's possible. Or I did mine as a browser based estimating system using JS as that is more portable between browsers then even spreadsheets are from one spreadsheet program to the next.
I'm not a fan of cloud and/or subscription services period, and given the nature of estimating and what the needs are there, this is one of the easier ones to migrate that to the cloud and SaaS is what's going to be at, that's for sure. I don't get that you have a problem with the cloud other then your worried about possible migration problems, I only mention creating own solution out of my own concerns with how software is distributed.
Other option is to use another service, if legacy files doesn't migrate (which like I said before I would be inclined to think that is more likely then using the same vendor for migrating) correctly, then VM the old stuff and use the new service for the new. This one or just VMing the older program would probably be your quicker options. Again, it just depends on how much time you want to spend on this and how much "future proofing" you want to do.
