Having a little bit of extra trailer will not hurt I would imagine, as long as you can move the axels to center the load. The new trailer I bought was of "the right length" but a little bigger would not have hurt. Also Cataumet Boats, since you are also in MA, was able to help me confirming the proper trailer size based off what they would have ordered. I only haul very short distances a few times a year, so the Venture was a good choice for me. I understand why people who trailer a lot would go for something different though. This is a picture of my 1999 on the VATB-8725 with target bunks. Brand new with Mag wheels $3770.
I got the rear of my bunks within a foot of the end of the boat. I emailed Grady and they said that was fine, the last foot has the tabs anyways and that wouldn't offer any extra support anyways. With it stored for the winter I threw the rear short stands under the transom, figured it couldn't hurt. Where you do not have the extended hull your boat should fit fine. The axels in this picture are moved all the way forward to balance the weight better.
