Up to $200 maybe more.
Meet other users.
2
Have my license.
Handheld.
Yes.
$200 each or total?
$100 each will get you Chinese radios. $200 each might get you something more on the commercial/durable side.
GMRS isn't too good for random contacts like CB or ham radio is. Users tend to use CTCSS or DCS code to block out others to keep communications just between families. There are some GMRS groups that are a bit more social, so finding one in your area and seeing what sort of radios they recommend might be a good idea.
If random contacts is your main interest, you would do better by getting your amateur radio license and an appropriate radio, or going the CB route.
Glad you have your license, that puts you ahead of a lot of other users.
Handheld will limit your range. Fine if you are outdoors, but consider an external antenna if you are using this inside.
As for the repeaters, it's a bit different that ham radio. Wide open repeaters are out there, but more often they are 'private' and the owner will want to arrange access with you ahead of time. Usually only requires asking.
But make sure you are in range of the repeater, and that the radio will support it.