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I've always wanted a boat,but have been warned by many: "The happiest days I had with my boat was the day I bought it . . . and the day I sold it." I stilll want a boat (mainly to go boat fishing whenever I want) but to me that would probably not be wise. But overspending on a car . . . well worth it.
yeah, boats are so impressive to other people but they are such a headache, one of my buddies has a 39" sailboat...pimp shit but so much maintenance.
The key to a boat is access. It can be a pain if you're transporting it from your yard, dropping it in the water, running around for a few hours and then having to haul it out the same day and dump it back in your yard. Winterizing it can also be a pain. Growing up, my family had a boat easement, so we only took it out in the Fall and dropped it back in the Lake in the Spring. Even then, it was a bit of a pain. My situation now is much better. Even though I'm rarely staying at my place in Oregon, my boat is in a boat garage year-'round and I just lower it into the Lake whenever I feel like taking a spin. In other words, the more time you actually spend on your boat rather than prepping it for use, the more you'll enjoy it.
That's it, I'm getting a boat. And I mean that not in a mocking way but in a way that I need someone to give me a push because I really want a boat. But since I can only afford to dry dock it (probably miles away from the river) . . . your words of wisdom doesn't get me there yet. Really what I need is to is buy a cabin by a lake and park the boat out there all summer . . . so ABM needs to add one more zero to this hypo and my answer is buy a lakefront cabin and then the boat.
Join a boat club? When I was in highschool, a friend and myself joined a sailboat club over by Jantzen Beach. I have no idea how much it costs now, but that might be a way for you to enjoy boating without actually having to do any upkeep.
Getting to ABM's question, if I had $100K tax free, what would I do with it? In the real world, I would just invest it. However, in the spirit of ABM's question, I'd probably pay for the second floor addition and renovation of our place in Colorado.