Originally Posted by rstackjd
The issue is how much should I have invested in a 30 year old Helms 25 and not get killed when it's time to sell and move up?
Hmmm...$3000 might be a reasonable number. So what you want to do is look around for a 25" with a new engine, recent sails, decent trailer, fully equpped with cruising gear, and give that seller the $3000...you'll get it back when you sell her. Leave the cheap boat for the newbie who doesn't appreciate how expensive it to get a neglected (no engine???) boat back into fully operational shape.
The point is you can't have a reliable, operational boat for cheap. trying to do so, ends up costing one thousands of dollars.