"It surprises me that there isn't better technology to integrate a modem with the SSB, such as an iPad app. I find downloading a Grib via SSB through a Pacor modem onto a laptop, then converting it into a readable file is WAY TOO COMPLICATED for the 21st century.
I need an app for that!! There should be a way to connect the iPad to the SSB, dial a freq and press a button. Seriously. "
There is. With Airmail and an ICOM 802 it is all automatic and controlled by pushing a button in the software on your laptop. Yes, you do have to make sure you are on a frequency that has decent reception for your location and time of day but the software makes it very easy.
As for the SSB ship station license - it does NOT convey to a new owner. You need to get your own. Whether the previous owner tells the FCC he sold the boat is not your problem - unless you think you can use his license and dont get your own.