If I was him, and assuming he's interested and has the wool over his eyes in regard to being married to you, my short-term concerns would be:
HIPAA How safe are my patients?
Backup and IT care of the server and network How safe is my data?
Getting his data if he wants a different EHR How hard is it to get my data?
Sounds like he doesn't have an EHR all picked out and that you could save him a lot more than $1995 in hassle and expenses.
