Harlan,
I am sure others can add their experience to your question; and, the answers can be particular to a specific site.
Many aviation training materials spend some time on orographic turbulence. The facts you state that you haven't had much experience with landing next to a windrow of trees, and no tailwheel experience looks like an opportunity for learning a new set of skills. Tailwheel training is part of it. Landing or taking off near obstacles, in my opinion, should be tackled a little at a time with easy stuff first (no wind and practice at fields a little further from an obstacle).
Generally, a crosswind where the row of obstacles is directly upwind from the runway will result in a downward roll of the wind and an apparent loss of lift at and below the obstacle top; and, the opposite if the obstacle is directly downwind of the runway. Even a wind directly down the runway with the obstacle row (trees) parallel to the runway can result in some difference of the wind speed from left to right across the width of the runway - all depends on the closeness of the runway to the obstacle, strength of the wind, height of the obstacle, etc.
I have used runways with obstacles of one sort or another adjacent to a runway. One in particular, with a high sand dune ridge next to the runway with the runway set down lower next to the water I just don't go to when the wind is coming briskly over the dunes.
It's not easy to figure out, we can't see the wind (so much easier if we could!) and the variables are great. A strong wind can cause surface turbulence a looooong way from the obstacle.
I like to see adequate clear space next to a runway; and, just won't land with an obstacle 5 feet from my wingtip.
Suggest some real life training with an instructor accustomed to teaching the ins and outs of dealing with wind and obstacles.
If it were me, I'd love to have a private 1000 foot strip; but I'd also mow down all of the trees anywhere near the runway and be done with the complication. Other than the trees, looks like a nice site. Another point to consider on a 1000 foot runway is to practice up on a longer one till a person knows for certain they can always do it.