So I guess I'm sort of asking: How do you approach your overall finances with regards to owning or even living on a boat and make sure you're not going to far? or not far enough (and end up annoyed because you didn't buy a comfortable enough home)? Stuff like that. Any advice appreciated.
Going back for a moment to the OP. We've gotten off into all our investment strategies, but back to your basic question, you and your partner must do what allows you to be comfortable. If it doesn't feel right, it probably isn't right for you.
I think one key is you don't make these decisions quickly or in a vacuum. You start thinking of them well ahead and you look at the numbers and you note the changes in your situation along the way. For instance, just in the last couple of years, your savings likely grew but so did the price of the boat, so you may reconsider what boat or decide savings grew enough to cover. Similarly, a rental or purchase home down the road has likely jumped in cost. You reevaluate for that.
You consider all the possible market shifts and health obstacles and also whether you and your family will enjoy as much as you think or thought. However, if any part of your plan really makes you uncomfortable, then reevaluate that aspect.
You're surrounded here, as in life, by people with far more and far less than you might have. Don't allow either to influence you too greatly. Don't pursue the dreams of others, just the life that works for you. Carefully think about alternatives. I know one couple that had plans for a larger boat and then suddenly it hit them that much of what they wanted to see could be done in a far more lavish motor home and they could rent boats around the country, maybe own one in their small home base. To them the simpler motor home life offset any desire they had for the water.
Discuss the perfect retirement with others, not just with boaters. We have close friends (and employees) who we recruited from our former home area in NC and their original thought was at retirement to go back to NC. They both grew up in the country on their parents acreage with cows, horses, pigs, and dogs. They enjoy boating but not like we do. Oh see them at work where they run our salons and you'd think city girls all the way. They just love South Florida so much they can never see leaving. They had a small home, fully paid for that was like the neighborhood doll house after all they'd done. Two black labs. Now, in South Florida there is an area called Southwest Ranches. Ranches not the size of Texas or NC, but horse lovers. They found an older home on acreage and more acreage beside it. They reevaluated their plans. The took on debt they never planned on. It means working longer than they ever would have had to but if they can go home each day to their "ranch" all is good. Alice is 50 and Rachel is 42. They decided they would rehab the house themselves with a little help. They have four horses of their own and board and keep 6 for others. They love their jobs and have found a perfect life for themselves. They get a total of 45 and 40 days of Personal Time Off in a year. They've taught the two 7 year olds in our family to ride, one who still prefers boating but one who loves time there with the horses even more and got her own black lab for Christmas. Alice and Rachel are at home covered with mud, grooming horses, tumbling with their dogs, hammering as they add a porch to their home, covered with paint. They love things we would hate doing, other than we love riding their horses. And, yes, they do have a Plan B. As they set down with us to talk about their plans, they knew I'd ask that. While prices may change, their property has at this point appreciated 60% in value between property prices in the area and the work they've done on it. Yes, two beautiful hairdressers supreme even built a stable/barn themselves. I've known them the longest of any two people in my life as started getting my hair done by Alice when we were both 25 and haven't been to anyone but her or Rachel since. I remember when Rachel was hired about three years later and Alice her mentor so Rachel at the adjacent booth. And I remember when we invited them to dinner about 20 years ago and they were shocked we'd figured out their relationship wasn't platonic.
The point is that Alice and Rachel have found the life and retirement plan for themselves. We also love they've taught Aurora and Juliet not just to love the horses and dogs, but what is involved taking care of them and grooming and even shoveling and sweeping the stables. When they go ride, they also do that part.
Boating is our love but not our only one and you need to balance all in your life and plan what works for you. Then don't be ashamed ever to change that plan if you feel the desire.