A couple of things need to happen - make sure that your provider (OTR) can support the Winegard by asking them to verify that the Winegard's IMEI number will work on their network. Second, the Winegard is considered a "Hot Spot" by the cell carriers, so make sure you have a Hotspot Cell Plan that is tied to your SIM card.
I thought I had read that T-Mobile supported Winegard. I don't know OTR, but if they run on the T-Mobile network, you can't assume that the SIM you got from OTR will work.
You cant assume that a SIM card that worked in another device will work on the Winegard.