50 miles is no problem at all for 2 meters, given a decent setup. I often work simplex that far away with my modest setup. Look up KJ7G on QRZ (me - just haven't gotten RR to change my username yet).
Simple Kenwood TM-V71a, with some LMR-400, and a Diamond X510a (3-5/8) omnidirectional antenna. I can work repeaters on Mount Lemmon, which is about 120 miles away from my home. That's just with an omnidirectional antenna with a 40' feed point. If I were in your shoes, I would go up that high at least, and better yet, 60-70 feet if possible (though you won't be able to do that as cheaply as I got to 40'). Put a rotor at the top, and at least an 11 element beam on a ten foot mast, and then an omnidirectional antenna about ten feet above that on the mast that at the top. Once you can at least detect a weak signal, you can spin your beam around and bring them to full scale. I have a neighbor with a 100' tower who does just that, and he has worked simplex at distances in the 140 - 150 mile range.
Now with that said, I would still suggest looking into HF, if you want range. You can talk to people all over the world in those bands. 2 meters is an great band, but HF is a whole other world in terms of range. That you should operate within the boundaries of the law and makes sure that you are properly licensed goes without saying.
Good luck.