Hi,
I am in my mid fifties and don't expect to be shopping for a trawler until my mid to late sixties unless lady lottery intervenes.
This won't keep me away from boat shows and living posthumously through the youtube liveaboard folks. My plan is for a 50-65 ft trawler to sail the Eastern US coast, Gulf of Mexico and the Caribbean.
I look forward to learning through the coming years as I lurk the forum.
Years to collect info......actually a lifetime....but
Don't wait until you have all the info, because you never will. Don't wait for the perfect time, because it will never come.
I don't believe in 10 year plans. It's fine to imagine 10 years ahead but I believe we're incapable of planning it. Too many things happen in the interim. People here have mentioned the bad things that can happen but good things can do. Maybe you will win the lottery or maybe you'll just find things you really enjoy. Maybe some opportunity will come your way.
If you want to boat, maybe you'll run across the perfect boat for now that doesn't require the lottery. You hear people talk about buying their last boat first, but that's mostly BS, as very few actually do that. We're not that smart, nor is it that time and place in life. If we wait to do that we miss so much.
You're in your mid fifties and intend to work well into your sixties, so my advice to you is to determine what you'd like to do in your fifties and do that. If it includes owning a boat, do it. If it's chartering two weeks a year, do it. If it's an RV you use occasionally, do it. If it's time with kids and grandkids, then do it. You can't get these five years back. When I was 30, I fell in love with someone smarter than me and I've lived life to it's fullest since. I can't get the first 30 years back though and I did a lousy job of living them. I worked, but didn't enjoy. I learned my lesson though.
I say think about five years, but in business I spend very little time on five year plans, just mathematically extend. The real emphasis is next year. So, I tell you the same thing I'd do for a Business Plan. Plan 2019 right now. Set goals and action plans. Figure out how to make it a great year and don't overthink beyond that. We've not even planned our boating for 2019 yet. We just decided to do Fantasy Fest this year and that's where our planning effort is going. We weren't even thinking of it two weeks ago, just decided. Enjoy life and take advantage as it comes to you.