A few things...
First, check the archives. There are MANY articles regarding the way an H23 should be pulled outta the water, how it should sit on the trailer (Your trailer is the stock trailer that came with the boat, so most of the advice in the archives is good), mast raising and lowering, and some improvements and tips for sailing this boat from people who've been through it. That said, I'll recap the common problem and solution for the bow not resting in the cradle when you pull the boat. When you back your trailer down the ramp, it's at about a 15-20 degree angle to the floating boat. Not a problem, this is normal... When you attach the boat to the trailer and winch it up good and tight, the angle between the boat and the trailer is still not the same- The trailer is at about 15 degrees, and the boat is somewhere around 7 (if you're lucky). When you pull the boat out of the water, the trailer and the boat level out, the keel makes contact with the lower platform, and the boat rocks back and pulls away from the winch/cradle assembly on the trailer by anywhere from 2 to 10 inches. THIS IS NORMAL!. There are a few ways of moving the boat forward into the cradle, and most of us who are willing to post a method believe ours is the best; You can search on any of the following in the archives. The popular choices are: -- Soap on the bunks, and winch like Hell. Personally, I think this puts undue stress on the bow eye, and you risk pulling out through the fiberglass. -- The "MacGregor Stomp" (My preferred method, when I owned an H23.) Search for it in the archives, you'll get the method in detail. -- Back the boat into a solid object until it moves forward on the trailer (NOT recommended by anyone, but one owner claims success). -- Pull the boat, put tension on the winch, float it again, and pull it again. Repeat until boat is where you want it on the trailer. (I did this until I discovered the MacGregor Stomp.) There are a few other methods, but these are the ones that immediately jump to mind. I've tried all of these except backing the boat into a solid object. One last item; There's a roller on the trailer that will not be in contact with your boat when it sits level on the trailer. 'Tis normal- The roller is there to help the nose of the boat ride up to the cradle when you are putting the boat on the trailer at the ramp, and to help the boat roll off the trailer when you launch it. If it works where it is, don't get any urges to move it... Also, check back here often! This site has a double metric ton of info about the H23- the archive articles on the H23 alone will keep you occupied for hours, and it's all good info. I learned more about my H23 here than from anywhere else, and the folks here genuinely want to help you have a good time with your boat- Sailing it, repairing it, modifying it, or whatever else. Congrats on your purchase, and welcome to the forum!--Jon BastienH25 'Adagio'(A Former H23 owner)