There are questions that tgrass is going to respond back but until then I will defer comment as there are many aspects to the problem. One is the ramp which he answered is not steep but moderate and the ramp is level sideways, not tilting.
On the tilting ramp sideways to include taking boats out when the water is high up on the road tilted as well above the ramp, the simple solution to get the boat on straight is to load the boat up on the high side of the trailer and it will settle down straight when pulled out. That is not the case in the original post.
Dennis also hit on a good point but might as well as discuss that now. First with the original post, the winch strap coming out must not be able to interfere in the path of travel not to rub against anything which is why I questioned the strap coming out on the bottom when coming out. If that is happening reverse the strap on the winch.
Tgrass also advised on new carpet and here I need to say one piece, not several scraps I have seen and needs to be outdoor and smooth.
The original photo shows a post coming up with a roller. That was factory installed and I removed that when a boat came in. I found that it hindered winching the boat up. It was on there to avoid hitting the crossbar of the trailer frame right in front of the winch stand. I elected to put a plate with roller to lower that down so the bow would not hit the frame. I have also seen delrin plastic used as well secured will and with the bolt heads not protruding from the delrin.
Now to address Dennis suggestion to include raising the struts or supports for the bunk boards. One of my questions was the swing keel (1 of 10 made on the 23 this way), did it clear the keel tray all the way or is it pushing down on the keel tray. If pushing down, those supports have to be raised so any swing keel is not being stopped by a keel tray when loading up from the water onto the trailer. With fixed keels I added rollers on the keel tray to help move the boat along on it as the fixed keels, the weight of the boats are on the keel, not the bunk boards whereas the swing keel boats are supported by the bunk boards. Dennis suggested raising the supports which I concur but make sure that the boat is level on the trailer when doing so as not to make the back of the masts higher on the back which might hit something when trailering.
There are other items that are on the market to put on the keel trays and bunk boards which might help.
However, in most cases the bow of the boat will not rest exactly where it should be. Why? The trailer is at a down angle while the boat being level on the water is being loaded up which is why I taught my customers the "bump technique." However there are roller style trailers which is out on the market and work great for getting the boat all the way up onto the trailer. However there are several cautions. Make sure when the boat is all the way up, lock the winch and also tie a line around the winch handle to the winch post so if the brake failed you have a back up. Also be sure that the boat is in the water and have a secure grip on the handle because the boat will roll off at an angle which I have always urged caution. In addition with roller style trailers, insure that a strap is over the cockpit but also the straps are led forward on the trailer some to insure the boat cannot roll backwards on the rollers. A good example is the trailer built specifically for the Catalina 22 Sport trailer by Roadking which one can even motor the boat onto the trailer. I was there when the trailer was designed.
As to guide on supports, if they are not straight up but angled out, that needs to be corrected to keep them from catching on something. In addition, if the posts are not long enough and a good example if the ramp is steep, they will catch under the deck to hull joint and a good example was Rgranger when I helped him trying to load his boat up as the ramp was too steep. Should it get caught under that, either the post and/or the boat will sustanin damage. In another case the posts were leaning out and the plastic portion too high as seen on Kermit's H 260. I straightened them out but suggested that he chop down the plastic pipes.
One other thing to consider is to check that the center supports for the bunk boards are all the way up so the bunk board in that position in the middle are also supporting the hull as well as many boat owners forget to do that.
Ok, my hands are now hurting and there is a lot to consider. I hope this helps