Wind drag is the major item using power when driving on a highway. I assume this drag is dramatically higher when pulling a trailer. Is it a 1.5x range reduction? 3x? Does anyone have and experience here?
There are several threads on TMC and videos on YouTube dealing with drag effect. Typically you can expect 20 to 40% of losses. In the case of roof rack or trailor hitch with bicycles, the measurements were done at 65 to 70 miles per hour. But in the case of a trailer, the speed was lower, like 50 to 55 miles per hour. In the case of a trailer, most of the comments were based on the Model X, but results should be very similar for the Model Y.
I pulled a 4x8' trailer with a model 3. Weight is less an issue than aerodynamics. A trailer loaded with flat boxes about a foot off the trailer (ikea flat boxes - wardrobes) yielded about 350w/mi while a squat rack that stuck out a foot above car height with 2 times the weight of the ikea boxes (1k lbs for rack + meat, some tools, ice to keep meat frozen, Olympic weights) + 2 kids, wife and a bunch of misc, yielded about 440w/mi...
I pulled a lightly loaded 5x8 UHaul box trailer with my MY on an 87 mile round trip. I averaged 370 Wh/mi vs 231 Wh/mi for the same trip without the trailer Speed was 55-60 most of the trip with the trailer, and 60-65 for the same trip without the trailer. If I did the math right, this means a range reduction of roughly 1/3. This is quite a bit less range reduction than what you'd get with most travel trailers since they have way more drag than the little UHaul.