There is nothing wrong with your plan. I would also suggest getting there early enough to spend some time in Glenwood on Saturday afternoon and evening. Hopefully you could leave the trailer at your motel and visit the start town expo and any other activities that interest you. It is part of the ride and at least a few of you would probably enjoy taking it in and if some don’t they can stay behind to guard the trailer!! Staying in a motel the first night is fine however, you’ll get all the camping experiences you want during the rest of the week.