Hello,
The O'day looks like a nice boat. Too much money IMHO, but it looks nice. I would offer more than $4K WITH the new sails. Anyway, the boats you are considering are ALL small. Really, learning on anything smaller than 25' should be easy. And you don't need to worry about capsizing like on a real small boat.
If the idea of boat camping or overnighting on the boat is appealing to you, then you should consider boats like the Catalina 22, O'day 222 or 23, Hunter, etc. A boat around 22' has a lot of benefits:
- Trailerable and can be set up / taken down by 1 person
- Spacious enough for 1 or 2 people to spend a night aboard
- Can have a porta potty / marine head and space for a camp type stove or maybe a marine galley
- Stable enough to handle decent wind
- Light enough to make docking / launching / recovery / etc fairly simple
- cheap enough for you to find a nice one for not too much money
- easy enough to resell when the sailing bug bites you and you want a bigger boat.
You should be able to find a nice Catalina 22 with trailer, OB engine, decent sails, etc. for under $4K.
Good luck,
Barry