I guess my question is, are cutter rigged boats a pain in the ass to sail or is that extra sail a benefit?
Not a pain to sail at all. Having an extra sail allows you to have more options when reducing sail and allows you to carry more sail area when the winds are light.
If you are in a position where you will tack / jibe frequently are there options like only running the staysail, removing the inner stay, etc? Can you run a big genoa up front if you want and basically be a sloop?
You can't remove the staysail stay on a hans christian, but you absolutely can just fly the staysail or genoa alone or just use the main by its self. Also some HC's have a boom fitted on the staysail making it self tending when tacking
If you haven't been there already check out Hans Christian Owners Association