Sailboat for a beginner - a couple of questions

A lot of good advise here. If you choose to build, buy plans from a living designer that is willing to answer questions if you find yourself in a hard spot during the build. Also look for building blogs for the type of design that you might build. Most likely, you won't be the first to experience the same difficulty. Steer clear of free online plans. Production "cruisers" in the size you are looking for aren't that common. The plans market covers the arena quite well. Here is a site with quite a few models in the size range you are looking for.

http://www.selway-fisher.com/PCup16.htm

Perhaps, there is the perfect one for you.

Good luck in the path that you choose.

 

Are Wayfarers still a thing? They were very popular a while back.

A colleague sailed one from Copenhagen to Helsinki for a honeymoon (staying ashore each night, either camping or in a hotel).
They are 4.9 m or so, and designed to be home built (in plywood).

Might also be available used.