jhogle,
The Trail-Rite trailers have an exclusive design. The tongue assembly is actually welded into the trailer frame at a slight downward angle. This helps tilt the boat a little making launching and recovering a bit easier, and helps out at a shallow ramp. Because of this, if you keep the tow vehicle attached, it binds, and just doesn't work. So, we've found that disconnecting the trailer from the tow vehicle, manually pulling out the extension out, re-pinning it into the trailer frame, and reattaching the extension to the vehicle is just easier and quicker. It really to have my 1ST Mate do the pinning because I have to giggle the extension a little to align the holes for the pin. So after the boat is rigged and ready to launch, we disconnect the trailer , extend the tongue, turn the motorhome around, reattach the trailer now to the front of the RV, and drive the boat to the ramp.
Also, contrary to may folks, I don't have a speck of oil or grease on my trailer extension. In theory grease and oil will help it slide, and yes it will, maybe the first couple times, but it quickly attracts dirt, and turns into a greasy dirty mess. Been there, done that, and I've been trailering boats for a while now....
My trailer and the extension are galvanized, and the boat has been launched 95% of the time in salt water. As you can see in the photos, the extension is still nice, and has not succumbed to rust, and I think the sliding action has kind of polished the galvanized surface over the years making it slide pretty easy.
Disclaimer: May not be what most folks do, or they've had different results, but it's just what seems to work for me.
Don