The short answer is yes you’re being way too conservative. Actually beyond conservative and into the realm of ridiculous to be worried about towing it across town.
The long answer is you’re also being way conservative using a wdh to tow a lightweight trailer like yours anywhere, even cross country.
The only reason having a wdh on a new HD truck to tow a 3 ton trailer would be for sway control and at that, only “if” the trailer has poor weight distribution and wiggles or sways under normal driving conditions more than a normal trailer would.
You’ve been towing for 10 years now, so if you don’t have the experience or confidence to hook up your trailer and just go for a rip to see how it handles without a wdh, then I’d suggest a small motorhome would be a much better choice for you.
There is imo a Very small chance you’ll hook up, hit highway speeds and think that it does not handle well. There is a great chance that you’ll ask yourself why you’ve been using a wdh with your new truck. Regardless of which way it goes, it will not be a dangerous venture to try.
