Congrats on the homestead.
As far as handhelds, I am sure you will get plenty of great recommendations here.
BaoFeng, Wouxon, Retevis, all make plenty of good GMRS handhelds at prices which will fit into your budget. Starting around $30 up to about $150. Just keep in mind Midland GMRS handhelds you can buy today are not repeater capable, so that will limit their effectiveness in your plan. They serve us great for "around the neighborhood communications." But if I had to do it again I would go with repeater capable handhelds, which I ended up buying anyway.
More costly options includes include commercial radios, Kenwood, Icom, Motorola. Its a steeper learning curve and plenty of folks here will remind you that most of the commercial radios aren't "legal" for GMRS according the the FCC. Just search up these forums for commercial radios, grab some popcorn, and read the heated debates about the legality of commercial radios. In the end no one seems to care, well maybe a few.
Repeaters, depends on what you want to use it for. The one you are looking at is a portable repeater that gets good reviews for what its designed to do. If you want a repeater at a base station with more coverage you are probably talking more in the $900 to $1200 range, unless you want to hold out for a deal on a pre-owned one.
Lastly, Don't take my word for it. Recommend you check out the "Not a Rubicon" channel on you tube for more info before you spend your cash.