
No, it doesn't sound right. Don't let anyone cut into your trailer. The worst that could happen is that your coupler need to be removed/repaired/replaced, any of which can be done through the front end of the tongue, by design.
There aren't a lot of things it could be here. You either have a loose fitting at the master cylinder or reverse lockout solenoid, a loose master cylinder cap or cover, or a punctured flexible line connecting the master cylinder to the steel lines below the winch post.
My original flexible line was too short and would be strained if I swung the tongue more than about 60 degrees. It never leaked, but it would have eventually. I had a new one made about 6" longer.
Before you have anyone go to extreme measures on this, consider that you can buy an entire new coupler for surprisingly cheap, and they're easy to install.