I have a squareback trailer with a 45 degree slope on front, and a flat back hatch. Basically a 4Hx8Lx4W square box, with the front cut down. I angled the front to match the height of my wife's old Cobalt's rear end (with factory rear spoiler), so she could tow it when camping (she never did, and I made it mine, after that). Of course, it ended up being heavily modified, over-stuffed, and exceptionally overweight, because that's what I do.
The trailer, being flat at the rear, needed something to break up the vacuum caused by the airflow over the flat roof. As a motorsports afficianado, ex-dragracer and car builder (mostly an assistant to a master mechanic/fabricator), I was aware of the use of various airfoils, wings, spoilers, splitters (etc) that could be used to change the behavior of the airflow. But, being cheap, and also unconcerned about the MPG incurred by towing a flat-backed trailer (because my tow vehicle gets 11 MPG towing any trailer, or none at all), I just used a simple raised bump (a rounded "Gurney flap "spoiler, if you will) atop the rear hatch (a folding piece of stiff conveyor belt, that also covers the open gap caused when the hatch is lifted), to break up the vacuum effect. After years of use, I've found that the rear hatch stays clean (a sign that the vortex behind the trailer isn't pulling in dust/dirt, which happens when the drag is high), so it must be working.
As for your design, I wish I had made mine the same, instead of the way it is now. I have to enter head-first, and exit feet-first, as my door is too far forward,and there's an overhead shelf over the 36" high door, so I must duck in. It wasn't too difficult when I built it at 61-63 y.o., but now, at almost 75, with bacd back, knees, and sciatica on both sides, I have to use grab handles to go in or out (or even to rise up from sleeping position). That's one of the reasons why I seldom camp anymore.
To avoid problem with an overhead vent, I chose to use steel, waterproof, two-piece vents fro etrailer.com, mounted in four places: two for cabin ventilation, one for supplying air to the rear storage area "galley" (and for cooling the interior mouted A/C unit), and the fourth for the exhaust of the A/C unit. I use the galvanized version of this vent

- Polar steel vent.JPG (60.06 KiB) Viewed 1057 times
now at $47 each, they were about $20 each IIRC, in 2012
I added bug screen mesh on three of the vents, and leave them partially open at all times, even in the garage at home. The one use for the A/C exhaust is basically a covering for the exhaust duct, and is lifted up when in use. The two vents for the cabin have 120mm Corsair computer case fans (that swing-away, if not needed) that can be switched to either pull air in or push it out, as needed. The vents have proven to be totally waterproof over the last decade+.