Here is my .02 cents. My first sailboat was an $800 O'Day Javelin. A great little day sailor fo me to home my skills on. After 4 years sold it for $800. Second boat was a Neptune 24 shoal draft, chosen for getting into quiet back areas to anchor for the night and easy trailering. I had the thought I would take the boat around the North West for summer vacations, that has not happened. After getting tired of banging our heads on the stainless pop top fittings 5 x a weekend we wanted something with standing headroom and an enclosed head. I shopped for 6 months and found a 76 Newport 28 which fit all of our criteria nicely. The boat is in good shape with many professionally done upgrades, standing headroom, enclosed head, decent performance and not a lot of unnecessary modern clutter. I prefer to feel more like I am camping than staying at a 5 star resort. We have a great group of sailing friends that all have GOB's we will raft up on Sat nights and have a pot luck and talk long into the night. It does not require an expensive boat to create life long memories.