Plane for Short Field, Grass Strip, Beginner?

Background:

I am about a 60 hour, non current pilot who hasn't flown in about 13 years. I have a pipeline coming through my place that has produced funds and this Summer will take out a clump of trees that will free up a place for about an 1,100 feet grass strip in the direction of the prevailing wind.

I solo'd in an Aeronca Champ and then did most of my flying in a 150. I flew once in a Hershey Bar Cherokee 140 and liked it, although it felt quite different than the other planes I had flown.

Question:

I would like to get something for under $20K that I can use for recreational flying and on a nice day, take my wife to visit her twin sister about 200 miles away. I don't need a fancy panel, just the basics. I don't need a real fresh engine because I won't by piling on hours at a rapid pace.

I will need a plane for the relatively short grass strip I described for daylight take off and landing. My idea is a 150 or a Cheorkee 140. I would love an old tail dragger like a Champ or a Cub, but they seem quite pricey and probably not well suited for a 200 mile flight with my wife.

I plan on using the plane for the instruction flying that I will need to get current again and will have an instructor work with me to get comfortable with my grass strip.

Any comments, advice and/or plane recommendations are appreciated.

Doc