I too use a handheld. From Oceanside, I can hit Catalina, San Clemente/Dana Point, Palomar Mt, and Keller Peak. All on 5 watts. So first question, do you really need 50 watts?
Your VHF antenna is close enough to 2 meters that it it should work. I would throw an antenna switch between the radios and the antenna. For 440, you can put up a dual band maybe on one of the spreaders. You really do not need much height with all these repeaters around.
Now if you want to go big rig, I use a Yeasu FT857D that has HF, VHF (6m and 2m), and 440. The output is 100 watts on 160m ~ 6m, 50 watts on 2m, and 20 watts on 440.
With your boat, you can put up an alternate backstay HF antenna with a good tuner and work 14300 Maritime Mobile Service Net.
The possibilities are endless. Good luck on the exam!