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I sounds very much like he has interference from some piece of equipment on his boat. For information on that, have them go to the Help file in the Airmail program and look for RF Interference.
The following description is long, but so you understand, here it is:
The problem that you describe is almost certainly an issue with RF interference-- transmitted signal getting back into your modem or USB/serial-port or computer and scrambling things. This causes Airmail to "freeze" because it can no longer communicate with the modem, and can also freeze the whole computer. This only happens when transmitting of course, and typically only happens on certain frequencies.
The first thing to do is check your boat's ground system, especially the ground strap from tuner to wherever it goes (keel, grounding plate, etc). make sure that all connections are clean, no "green crud", etc. A bit of surface corrosion is not a problem, but connections must be clean and tight. Copper tape should be soldered at each junction.
Also important is number and location of ferrite chokes, the clip-on "ferrites" that should clipped around each end of the cables from computer to modem to radio. Look up "RF interference" in the Airmail help file for details (Help menu, Contents, click on "index" tab and type in "RF interference"). The ferrites work in conjunction with your ground system to encourage the transmitter signal to go where it belongs (to the boat's ground) and block it from going where it shouldn't (modem, USB or serial cables, computer). If you don't have any ferrites then ask among other yachties, many folks have spares- or try moving some that you have to the serial cable to the serial and/or USB cables between modem and computer. The problem may also depend on whether there is a ground connection to the radio- it is generally not needed but can make things better (or worse) of there are deficiencies elsewhere.
If this is a new problem-- or an old problem getting worse- then look for corroded connections somewhere in the ground system, or possibly in the wire from tuner to backstay.