Most trailers 20 feet of more can be sufficient for hauling the car. The bigger you get the more space you have. Cabinets, floor covering,escape doors, generators, etc. all add up and can push the price up quickly. What also needs to be addressed is how comfortable are you driving and more importantly parking the setup. I’m fair at best and I usually research where I’m going for spaces big enough for me to park. I google earth the hotel, look at restaurants, and even gas stations to make sure I can get in and more importantly out of the space. The turning radius on some truck/trailer combos are quite daunting and the height is another restriction
The more you drive it the better you become. If you do get a set up practice driving around in a large parking lot with cones and marked off spaces to become proficient with the setup. I know people who tow with the F150 ecoboost and have no problems, Ford offers a ton of options for towing on the F150,camera setups, auto backup, heavy duty cooling and towing packages. I also have friends that tow 28 foot and larger trailers and they all have turbo diesels and the torque of those engines are amazing, but the cost for initial purchase and some of the up keep is somewhat expensive.
I change the tires on everything when they hit 6 years old, regardless of how it looks, seen too many tire blowouts from tires that have aged beyond that. I also carry two spares in the trailer and check brakes, lights, and use an infrared temp gun to check tire and wheels temps when ever we stop.
I might be paranoid while towing but since it’s the car riding in a trailer I don’t feel too much safety is too much.
I have only towed the car to three shows, once to Carlisle for the 50th Mustang celebration because it was going to be displayed inside and they were calling for torrential rains, SAAC 42 because my wife said she’s getting too old to ride that far in the car and the 2016 MCACN Show in Chicago in a November because, well it’s November in Chicago
I have towed other people cars, moved my daughter 800 miles and even moved flowers for a wedding with the trailer all with no problems or issues
Since I don’t have a garage, the car sit in the trailer, I keep both heavily insured. The trailer has alarms, 8 sets of locks and even a boot to make it extremely difficult to move or break into
With all of this, it’s one of the reasons I prefer to drive the car to most shows
235,000 miles and counting on the car