Others may have a different opinion.
I would start with a very standard radio
install either Ham and / or marine SSB
depending on your needs. In the case of Ham radio
that means a backstay, ATU and radio to suit your preferences. Read the various boards and make sure you concentrate on DC power and grounding. I would be tempted set up a secondary back stay arrangement and to not cut your existing back stay until you have a better idea of what works for you and your boat.
For some considerable time your going to need to acquire operating skills. Do your study course and read lots of extra material on operating and propagation. Once you have your licence and everything installed build up the hours in front of the radio learning
what works. Many of these early hours should be spent listening... eg listen to the 14.300 net and you will often get some really good examples of operating procedure and the practicalities of propagation.
I suggest a good operator with a mediocre radio will still get much better results than an inexperienced operator with too many buttons and knobs to play with.
Train those ears and learn the procedures and courtesies and you will have lots of very satisfying QSLs.