My recommendation would be to get a ham license and a transceiver that can operate on both ham and marine bands. Herb uses a marine band (ITU ch. 1253 or 12.359 Mhz). He does this with a somewhat unusual license to operate from land. (He started out doing this from his boat anchored in Bermuda) If you are going out cruising in the Atlantic/Caribbean access to Herb for weather routing is very important.
With a ham license and a Pactor modem, you have FREE email worldwide. With Sailmail it costs but you can run your business remotely. If you have any ties to shore, email becomes very important after you are gone for a while.
The solution that minimizes the equipment complexities is just a marine
SSB and Sailmail. Except this is the expensive route.