I think you hit the nail on the head when you said you were looking for the simple life. Unfortunately, looking after a boat can be far from it. I am considering living aboard. I would always try to use the KISS philosophy, keep it simple stupid. Boats can be complex and very $$$, but they don't have to be.
My wife and I bought a remote place in the woods just after we were married. We had no phone, electricity, just the dream of running a small outfitting business in the summer to pay the bills. Life got in the way. We started a family, took a mortgage to pay for modern convienences like generators, solar panals, running water, wiring, and additional space for the kids. Well mom needed a good 4X4 to work out and pay for the mortgage. More stuff and more stuff was needed to maintain the the "new" simple life. We started out with oil lamps and a wood cookstove and happy. We ended up with all the expense and trappings of modern convienences which in the end we couldn't sustain. After 10 years we sold out and moved into town. Now I feel like I'm living in a hotel room. Remote controls, no wood to chop, just flick a switch for this and that, how real is that. My new boat is bringing be a bit of sanity back.