The Breaks is a love it or hate it kinda place. I personally love it and have spent a total of several years up there. We spend most of our time on the other side though. If you were in Winifred and went down to the ferry (stops running soon I think), cross the river and roam your way towards Chinnook or Big Sandy through the Bear Paws. BTW, there is a surprisingly mean burger in Winifred at the bar. I can't tell you much info for camping on the route you're headed on but if its like the rest of the breaks, you can probably just pull over anywhere and nobody will bother you. You can also most likely pull your trailer if you don't mind giving it a workout like I do. The thing you really need to watch this time of year though is rain. Maybe you're familiar with Gumbo? It doesn't take much moisture to turn it into a sloppy mess out there that only an ATV with chains can get through. As we get closer to winter if you get stuck you can just wait until morning to get out when the ground is frozen. Its dumping rain where I am just east of Missoula right now, not sure what its doing up on the hi-line.
NOTE: If you have dogs, there is a mean case of blue green algae going around this year even in flowing water. My sister in laws pup died within 2 hours of swimming in the creek a couple weeks ago. Also, much like eastern washington, it can be littered with rattle snakes out there.
As for elk, if you know where to look they are everywhere out there. Not sure if you want to see them in the wild or if you're just heading to Slippery Anne, though even at Slippery Anne they're gonna start heading for the hills fairly soon.
Browning can be fun if you like to booze it up with some rowdy natives, but for the most part you're gonna wanna keep moving. In fact all of the reservations in the areas your going can be rough. Rocky Boy, Hays, Browning.
Have fun exploring. The sunsets/rises and stars in the breaks are hard to beat. You're covering a ton of ground in only two weeks. If you find yourself heading through Clinton on your way to Helena and want a place to park for a night, send me a note. I live up Rock Creek.