Few things seem to get more negative posts on this site than towing tandem. People usually come out of the wood work telling you that you are a danger to society by doing this, an accident waiting to happen, and are quick to tell you laws from some on line souce (that is usually inaccurate), and that your insurance isn't going to cover you when you inevitably cause an accident.
My experience is that if you are set up correctly, and drive responsibly, and plan ahead, your trips will be trouble free.
As I stated earlier, I have been towing tandem for years (probably more than 15 now). I had a custom welder fabricate a hitch when I first bought my current 5er new 13 years ago. And the 5er before that had one as well.
Towing lighter weight trailers I don't even notice that it is back there. I have a 16' aluminum fishing boat, probably weighs around 2500 pounds (likely less). I can't see it back there, so a rear camera would be nice, but it isn't needed. The difficulties can be when you need to get fuel (why I have my aux tank), when you are going into a tight campground (when going to a lake, I drop the boat off at the boat ramp parking lot on the way in), or if you get into a situation when you need to back up (that can be big trouble).
Bigger trailers are a different story. I also have a ski boat. Old one weighed about 5500 pounds, new one is closer to 6500. With a lot of tongue weight, all the expansion joints in the highway, or any rough road, are amplified up to the truck. There will be a lot of chucking, and a ton of stress put on the trailer. I actually broke my hitch last year (not a catastrophic failure). This year I had the hitch and back of my RV beefed up to the tune of nearly $2000.
After all of that, I decided to take a 2nd vehicle when pulling the big boat. Still do the small boat without thinking about it.
You sound like you are considering a smaller trailer, which I don't think would be much problems. My take aways are as follows.
1. Spend money on they hitch with a quality fabricator. Not a bolt together job.
2. Consider adding an aux fuel tank or replace standard tank with a bigger tank in the truck if you are going off the interstates
3. Some sort of air ride will improve the ride in the truck. I added an TrailAir pin box. If I were starting over, I would do true air hitch in the back of the truck.
4. Always plan ahead, know where you are camping and fueling. I have seen people back up, but I have a hard time with it.
5. Rear view camera behind the 5er woudl be nice, but not necessacary.
6. Tandem axle utility trailer will tow much better a single axle
And, perhaps most importantly, ignore all the naysayers out there, and be safe and have a good time.