On a practical note, backups
backups backups backups BACKUPS might be the only thing that can save the business. Make sure they're automatic, cover everything critical, and are offline/offsite.
More significantly, any modern servers are going to be a problem because without hoop-jumping they won't talk the same protocols as very old PCs. This will also be a problem for browser use (missing support for newer encryption methods, lack of
any supported browsers), etc.
Edit: And I don't think "XP" and "up-to-date AV" can coexist these days.
On a more personal note, if part of the problem is health insurance then the exchanges aren't great but they're mostly not terrible either. Open enrollment just ended but you wouldn't have been eligible anyway, but if you leave your job that was providing health insurance that triggers eligibility for a Special Enrollment Period.
You may qualify for a Special Enrollment Period if you or anyone in your household lost qualifying health coverage in the past 60 days OR expects to lose coverage in the next 60 days.
(
https://www.healthcare.gov/coverage-outside-open-enrollment/special-enrollment-period/)