I've never heard of AmiPro, but I'd be surprised if any Windows 3.1 program (that wasn't driver-dependent) didn't run perfectly under Wine. Definitely worth a shot I'd say.
As for hardware and software support... when was the last time you called up Microsoft and they actually were able to help you solve your problem? I'm sure it happens on occasion, but every time I've reported a problem in their software (such as a ViewMaster monitor which was always detected incorrectly by Windows XP as a TV upon boot and made the screen low-res and all green), Microsoft's never done squat to fix it.
Contrast that to GNU/Linux. I ordered a Bryton GPS cycling computer, and assumed it would support GNU/Linux. It didn't, my bad. Fortunately, I found somebody who wrote a driver for a similar model. I gave them the specs of what I had, and they whipped up some driver modifications to get my device working perfectly - just to help a brother out.
Somebody got LightRoom working under a patched version of Wine and shared the details. If you upgrade to a new version of Windows 3 years down the road and LightRoom stops working, do you really expect Microsoft or Adobe to support you? I be the Wine community would. There is support, and then there is support.
You get my point.