Pragmatically you divide this into sections.
Finance- two major divisions.
1. Income stream when cruising
Rental income (then need to deal with management so deduct ~10%, assume need to deal with periods it’s unoccupied so need to assume carrying costs and need other sources etc.). We went with no rental income
2. Consulting or remote work. Beyond simple things like VPNs issues of having adequate communications and ability to leave the boat in short order for indefinite periods of time adds complexity. We went with being only dependent upon investment income.
We went with a plan that put nearly everything on autopilot. Between establishing a close team (accountant, financial planner, lawyer, family) we could have everything run on autopilot in our absence. Scheduled phone calls once a week or every two for some things meant we could focus on cruising and not worry about income stream or other things. Remote monitoring of assets occurred when we choose to do it. We also had a very reliable estimate of available funds which allowed conservative choices in boat, discretionary expenditures, and cruising plans. This level of reality check is required for sustainable cruising. But everyone I know who had a non investment income stream had some level of not having thrown off the chains. Rather at some level were working remotely. This created some level of stress. It also effected cruising plans.
2. Taxes- where will you declare residency, how will you establish income stream hence tax liabilities etc. how will you make this totally autopilot so quarterlies and other liabilities are addressed in your absence. If you go off the grid and don’t just marina hop this needs to be on autopilot. Inevitably communications will fail at just the wrong time.
3. Communications- this is huge. In spite of having WiFi boosters, satphone and data, SSB and vhf , local and international and domestic chips this was always a hassle. You need multiple ways to have secure communications to run financial affairs. You need multiple ways to stay in touch with advisors, friends and most importantly family. This was a significant expense in our cruising budget. A mail service and in our case a family member with power of attorney and an financial advisor with limited power of attorney worked out well.
4. Health care- this is determined by where your cruising grounds are expected to be. Health care in the Caribbean is dismal. I’m a doc and wife an RN so we have a leg up in avoiding need for outside care. Even if you don’t have that background a few s courses in wilderness medicine is a great idea. Add in knowledge about local diseases (for us it was local tropical medicine) is very much worthwhile. Medivac insurance is a must. Even if domestic if you’re laid up you want to be wherever you have access to family, and your network.
5. Boat selection- what you think you need and what you really need are two different things. I had been ocean racing and short term cruising for decades. I was totally clueless about the details required for long term cruising. I could write a book but suffice it to say.
KISS is BS. You will miss long hot showers, cooking gourmet meals, having a comfortable environment in your boat and all the various comforts of home. This adds complexity, knowledge base, maintenance and expense. But happy wife happy life. But the belt and suspenders principal still holds. We planned and outfitted to be as totally self sufficient as possible. We educated ourselves to achieve that goal. At just about anytime we could go ~ a month without putting our feet on the ground. Limiting factor was food and restocking spares. Regardless of how large a boat you have space is always an issue.
All the above is determined by what your dream is. Ours was cyclical travel from new England/maritimes to primarily leewards. We dislike tourist destinations. We like remote areas. Others seek ICW snowbirdiing or RTW doing the clock. It’s a back and forth. What’s your dream v can you do it. Just suggest write out the dream. Discuss it with your significant other. You need to be heart and soul on the same page. Do the math and take a cold hard look at yourself. Then judge what’s practical and achievable. My dream was RTW (round the world). After going through the above exercise decided not to. Two areas of failure. First wife wasn’t as invested in doing it as I was. Second, unless you’re on a crewed mega yacht with access to a Challenger 350 that’s what you’re doing for several years. It a big commitment. I wasn’t sure I wanted to be that limited. Wife was right on this one.
