Looks like this thread hasn't been used in a while, so here's my story.
I grew up on a large farm in SE Wisconsin. We farmed about 3,400 acres and had about 300 pigs and 60 head of beef, and grandma had her 30 or so chickens. We didn't have time to do much for outdoor sports/activities outside of farming. We had a guy that would take us salmon fishing on a charter boat in exchange for hunting on our land. That was about the extend of my water/boating experience growing up.
Fast forward past college. My best friend in college (and still my best friend) both got a job in the Green Bay area, so we were roommates again in the real world. Two single guys living together did not help us 'mature' as we were bad influences on each other and kept partying like we were still in college. Fast forward another 2 or 3 years, and my roommate's older brother bought a 20' open bow boat. We would head up to Door County almost every weekend to 'go boating'. Cruising around the bay, anchoring at Nicolet Bay at Penninsula State Park, heading to Chambers Island, etc. was so much fun. We would be out on the water early in the morning to sunset. The sunset over the bay is absolutely gorgeous.
My roommate's brother is a mason and when the economy tanked in 2008, he fell on hard times as the volume of construction dropped and he sold the boat.
Fast forward another 5 years. My wife's mom was diagnosed with cancer and they had to take a large lump out of her leg. It was so big that she lost a lot of muscle and now has a hard time moving and getting around on anything that is not paved and flat. A few months later, my mom dies unexpectedly during a knee replacement surgery. Both my mom and my wife's mom were close to retiring when these events happened. Both had planned on doing more traveling after retiring since both of them didn't have much money for 'play' up to this point.
After these events, my wife and I both talked about how to make sure we enjoy life while we can without making too much of a sacrifice for the future. I brought up that I enjoyed being out on the boat. We were going to buy a boat. We discussed it and bought a mid-eighties 18' open bow Sea Ray for $1800. It ran, but was fairly beat up. The point of buying this boat was to make sure we both enjoyed it, could learn the ins and outs of boating, docking, launching, etc and if we it the dock a little too hard or anything and scratched the boat, it wouldn't ruin everything. The first couple of years we used it about as much as we could. The trailer wasn't in good shape, so we didn't feel comfortable towing it any significant distance, so we stayed within 45 minutes of where we lived. One beautiful Saturday afternoon, we were docked at the City Deck in downtown Green Bay, and our boat was struck by another, larger boat where the guy claimed he tripped and accidentally pushed the throttle forward while he was coming in behind us to dock. Long story short, our boat hit the dock hard enough that it damaged the transom and we were taking on water. The bilge pump could keep up, but it never shut off either. It would cost us $6000 to repair. While we had some awesome memories of this boat, it wasn't worth it to fix an $1800 boat. We went without a boat the next summer (2018).
Fast forward another couple of months, my wife takes me to the Green Bay boat show and says that she wants a pontoon. She misses being on the water. She wanted something a little more universal where we can go fishing off of it, just take it for a cruise, have family and friends on it for some fun, etc. We now have one on order and expect it in late April. I usually don't wish time to go by fast, but I am so excited to be getting our boat.