I would suggest the only reason the boat is sitting in this location is because the last owner didn't want to move the marker light. From what I can see in the photos the winch and roller need to move aft about 6" or so. I agree that the transom should be inside the end of the bunk by only a few inches. I would be surprised if this change had a significant impact on the tongue weight, but again be mindful of the results. As for the speedo pickup, I wouldn't let it bother you just yet. Mine gets caught up on the bunks every time I pull my boat out if I'm not perfectly aligned... And that happens often enough. Between its flexibility and the adjustment to your trailer, you should be ok. If it breaks, get a new one and relocate it.
At the end of the day I think the time you spend upfront to setup the trailer properly will reduce your stress at the launch. Boats were designed to reduce stress not create it!
I also recommend vertical guide posts. I trailer a lot also and they helped make launching and retrieving my boat a breeze this past season.
Here is a link to a few methods of confirming tongue weight.
https://www.etrailer.com/faq-how-to-det ... eight.aspx
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2004 - 288 Vista
Twin - 5.0 Volvo Penta GXi DP
