Which version are you using?
I previously has v13 running smoothly on my Win10 PC (no VM) and had for about a year. But something in the last 3-4 months windows update-wise has borked that and now anytime I try to get into monitors it crashes to desktop without an error message. I am assuming this is probably a driver incompatibility with the older version of TIS.
My solution was to go back to v12.20.024 that I had laying around and install that. Everything is working perfectly now and I can get in and out of monitors, utilities, etc. without issue. From some other digging I have done, it seems that v13 had stability issues with Win10 that are known on the professional side. Apparently this looks to have been corrected in v14, but don't know how hard that is to get your hands on. For my 98, v12.xx is more than adequate as I don't have any of those items that allow for customization.