If you search for "long range repeater" using my username of "
miraculon", you will find several posts about my experiences regarding a very similar situation.
The trees are indeed a concern, especially when the leaves are wet. You also have houses in the signal path, the same as I do.
I suspect that you are going to have problems at that distance. You can look at my setup at the bottom of
this page. I have a 3rd party Yagi with 17dBi gain, a mini-circuits preamp and band-pass filter for the 902-928MHz range.
My situation did not allow for a 2nd long-range repeater, but since both ends will be under your control, you could put repeaters at both the sending and receiving side.
I have had reasonably good luck with my current configuration using the 17dBi Yagi, preamp and BPF. (I do get an unexplained interference that reduces my "good packet" rate, but I have never lost signal with the current setup). This took several iterations and a lot of experimentation to get it to work.
If you need/want more details about what I did, I would be more than happy to send information. Just PM me and I'll send info.
Greg H.