You have the trailer in too far. With trailer out more, the front of the boat will lift on the rollers and the d ring will go between the bumpers. Plus, it's a lot easier to power up onto the trailer with your engine, but some places frown on that because it undercuts the concrete ramp. You've probably already learned the perfect depth to put the trailer so the boat centers itself automatically. Believe me, I've spent a lot of time doing exactly what you were doing there!

Thanks Karl. I’m getting ready to haul out my 25 on a trailer for the first time. I didn’t know about a tongue extension. That looks like it’s the way to go.

The commentator sounds like the French Drain Man from Michigan. A good guy.

Now that the boat is on the trailer, prepare trailer for the next time you have to recover boat. First: use a wood 2x10 by 10 feet long TREATED, cut off two each 6 inches long and then cut rest in half so you have two lengths 4.5 feet long. mount on one end at an angle, approx 45 degrees, one of the 6 inch pieces, on each length With deck screws mount on each side of trailers keel bunk, at the keel location, with the angled pieces towards the back of the trailer as guides to center hull on trailer, first time and every time after. The angles will help guide the keel onto the trailer perfectly. Modify your winch set up to only one bow chock. The center bolts that holds on the double chock bracket, remove and take one chock and mount on one long bolt through this centering bolt holes. raise or lower the whole winch set up with the two U-bolts holding it onto the post to make the hulls eye bolt just touch the bottom of this one chock for perfect positioning every time.

Lowering the mast to aft. Yup I did that the first time with my 25 ft Oday, went to far down and the mast rested on the hatch cover, it acted like a lever and snapped my mast bolt heads clean off. That wont happen if you lower it to the bow.

To help on haul out, keep your bow line over the bow support on the trailer so you avoid pulling the boat towards the dock. You also need to have the trailer out of the water more at first so it keeps the boat aligned on the bunks. As you need to bring it closer to the bow support you then can back into the water more.

Ive yet to put my 26 in the water. so far Ive seen this is what I need. 1. at least an 8ft tongue extension. 2. side guides mounted to the trailer to ctr the boat on the trailer.

You'll get the hang of it Karl. Launching is pretty straightforward. Retrieval is much more nuanced ... ;~P Now, let's try to get that mast lowering time down a bit! No worries, you'll develop a solid system for both.

Our Oday 25 was in the water when we bought it , no trailer. I had one made for it so I could bring it home to rebuild the transom. I had to fit the boat to the trailer at the ramp. Of course a cold rainy day and everyone wanted to help ( in the way ) . After about 2 hours of it will not fit , this trailer isn't made for this boat , etc. all the help left, which was okay with me. I accessed the issue and kept cutting the bunk post and loading the boat on the trailer. After about three more hours the boat was on the trailer sitting on the bunks and keel. The former currious help would come by during my time alone working the issue and cast their words of doubt and doom . My trailer has a permenant extension welded on , it makes handling it tight places much harder. I like your roller trailer, easier to paint the bottom. I have 16 ft bunks and I have no way of painting under the bunks. I know there are ways , but our boat is on a sandy hill leaning downhill on the port side. If it were on level concrete I may attemp to lower the bunks while supporting that side. Your boat looks nice . I repainted the hull and the lower stripe look like a drunk did it.

6:11 trailer way too deep always entertaining at the ramp

A roller trailer doesn’t need to be backed that deep into the water, the boat will better self-align if she is being winched onto the rollers, not floated on. Might have been much easier unstepping mast if you used the original instructions from O’Day and lowered the mast forward as designed.

You should check out channel, Sailing Dachaidh.