I have a '48, the weight is abut the same as a '55. I have trailered it several times with my 16' car hauler pulled with my '99 GMC pickup. Pickup has a 4.8 liter engine - the small V-8. One trip was 250 miles thru east Texas. "48 Pickup about 3500 lbs
16' carhauler 1200 lbs
GMC pickup somewhere around 5000 lbs.

Your Youkon is slightly heavier that my 99 pickup
Your Yukon engine is larger than mu 4.8 V-8
There is no reason your Yukon could not pull the trailer with the 55 on it.