Sounds like a ton of fun. I'm jealous.
You'll do fine with GMRS radios of any measure on your property. If my mental image of your agricultural property reflects reality it's going to be no problem for a kit of straightforward HTs doing simplex. Maybe all choose an agreed upon frequency and a tone as a family, just to sort of have "a private channel".
If you want to get a repeater up to get off of the farm and into town, just do that Retevis thing and make yourself a nice mast up high somewhere. It's all about height. Higher the better. If you want to get out further, figure out how to get it even higher. Don't sweat radio power. It's the most overly discussed aspect of things on UHF radio, and it's almost not even a factor. 5 watts up high beats 50 in a hole all day long..
Another option for an ULTRA cheap repeater is a simplex repeater. It's just a real simple deal. It's a box that connects to a radio that you just set out somewhere (again, preferably really high), and it'll just sit there in the middle of comms, and record everything said, then spit it back out afterwards. They can be annoying if you're in range to hear both transmissions, but they do work very well and the simple nature of it means there's not much that can fail. Easily and quickly deployable for temporary type things. It could be a short term option if you don't want to spend on that full duplex repeater box quite yet..
You could get all of this done on just a couple hundred bucks worth of Chinese stuff..