I would highly suggest that you try a much simpler configuration first. After that, if you are not satisfied with the result, you could experiment etc..
I doubt you will get much of a difference in numbers if you simply place your Anemometer up on the Roof and mount your ISS as a whole on a post at 5-6ft. No Alter style wind break, no PVC pipes (most likely will bend and sway anyway).
You are going to a lot of trouble to be perfect with what I think will end up being negligible different results from a more common simpler setup. This is especially true when you factor in the accuracy of the instruments and issues in your area that will effect your sitting location (Unless you plan on cutting down some tree's too).
I don't want to have to add a wireless unit to the anemometer. The solution I propose only requires a cable from the ISS to the temp sensor, nothing else as the other cable from the anemometer to ISS is provided and is long enough. I don't know of any other way to put one thing on the house and the other 75 ft away in the yard other than a long cable and trenching it into the ground?
I don't consider it a lot of trouble and your suggestion still leaves the issue of mowing around it? PVC pipe is pretty sturdy if a big enough gauge is used and there isn't much sway 2' up the mast???
I didn't say where I would mount this so trees might not be a factor. Actually, trees are no more a factor where my current mast is than on the house...actually, there are taller trees closer to the house (and taller than the house) than where my current mast is. I am still considering mounting this out in the field away from everything.
The PVC pipe is cheap and stronger than I think you think

Go to the hardware store and grab some 3 or 4" PVC. I bet you couldn't bend it. I can't

and the time to do what I am proposing is probably less than the drawing took to make

If I thought it would take a lot of time, I wouldn't be doing it.
I was going to initially install it on my current mast and see if the plan works, then install it on a stronger, taller mast when I see if the concept works.
Thanks for your input!
Lew