Originally Posted by Xx Darkwing xX
Sadly the whole wants vs can afford to have issue is rearing its ugly head. Being new I don't want to go to big and end up not enjoying the boat yet I contest to get an older boat and be forced into serious maintenance issues. I think I wants 35-38 lot Catalina, maybe beneteau at this point. Maybe as old as 92 ish.
I wouldn't assume that an older boat means forcing yourself into serious maintenance issues. A 20 year old boat can easily require serious maintenance if it hasn't been kept up - twenty year old rigging, sails, engine, upholstery etc. are, or can be at the end of their lives.
There are LOTS of old boats that are in perfect condition and lots of quite new boats in need of serious work - see an ex-charter boat for illustration.
It sounds to me that an old Catalina 38 (The S&S / Yankee version), if well kept, would be ideal for you. There are currently 15 of them on YW, asking from $20K to $55K. Picking up one of them for say, $32K and spending some more for new sails, running rigging and upholstery will still bring you in well below a comparable used boat 15 years old. The condition of the engine will be a critical point in which boat to choose though - that can get REAL expensive.