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google earth is your friend. you can map point to point save and look at elevation detail in between 2 points.

PM sent w/that in mind I did a quick mapping. at 30' at your location and 20' at the other 2 unknown locations. based on the 40W radio as mentioned w/50' of cable at 1.5 dB of loss and a 5 dBd omni antenna. terrain elevations vary as much as 200'+ , you being the hole in the donut. you might just get away w/it but the mapping isn't fool proof, its just a rough esimate.

what you need is an elevated outdoor antenna at each site. 16 miles is easy over flat topography with each site using an elevate antenna. you will get more for your money upgrading your A.S.S. than a higher power radio.

I have the Midland 115 for mobile use. It works great and I hit a repeater that is more than 40 miles from my house here in NE Georgia. That being said, I also use a BTECH V1 hand held that hits that same repeater. I lived in Corinth about 10 years ago, so I know the topography of the area. What you plan on using should work great. I would suggest not using the repeaters. Pick a channel that all of you could meet on. Set up a PL tone for all the radios. Don't use 141.3 as that seems to be one that is favored for most folks. For antennas go to the website " antennafarm". I have not bought from them, but their reputation is very, very good. If any of your stations have HOA that prohibits outside antennas, then Antennafarm has something that can be used in a attic space.

First of all, thanks for joining and asking questions! Your existing GMRS license will cover all of your family members: parents, brothers, sisters, grandparents, aunts, uncles, cousins, inlaws, and even outlaws... <just kidding on the latter> If you are interested only in base comms between houses, the Midland (w/power supply), and an antenna ~20' elevation should do the task well even in simplex mode. You might wish to look at the WLN-CD1 portable radios available from Amazon and elsewhere. For $15 each, they are prefect for repeater coms, or local simplex use. They are perfect for younger children as well.