[Destroyer]

First off, I agree with everything that Tsubaki just posted.. Now, lets take it back even a step further.... You say in picture three that your "eylet still gets hung up on the lower support when you try and winch it in". I'm confused. (Don't worry, that's normal for me) What eyelet? Do you mean that the bow eyelet that you connect your winch cable to gets hung up on the first trailer crossmember as you start to winch your boat in? If that's the case your trailer isn't in the water far enough. Simply put more of your trailer in the water. At the very least your rear lights and the first crossmember should be totally submersed. Ideally, your boat should actually float over the first crossmember and then make contact with the rollers.

Looking at your pictures it appears that your winch is slightly (not overly bad, just slightly) low. The top of the winch and the top of the bow eye should be the same height when the boat is completely winched in and at rest in the stops.

Looking at the picture of the side rollers under the boat in the back, they appear to be properly adjusted to the width of the boat. I don't see them contacting the lifting steps on the hull anywhere, so the boat should just roll in nice and easy. Are there center rollers along the entire length of the trailer or just at the front where you had one put on?

If they are just at the front, and presuming that both your front and rear side roller brackets are set to the same height, then I would suggest that you lower your rear set of rollers one inch. (Usually the brackets that hold the rollers to the trailer crossmember will allow for 3-4 inches of up or down movement for adjustment in one inch increments) That will make the bow of the boat lift as it hits the second set of rollers, (the ones closer to your truck) and will give you extra clearance as you come to the front tongue and the rollers you had put on.

A boat should want to follow the winch line up the trailer like a puppy following you around.. It shouldn't be a job or a chore.

Send us more pics of the underside of the boat where it contacts the trailer, the overhang of the boat off the rear of the trailer, and the rear crossmember of the trailer.

Oh...one final thought. If for some unholy reason the trailer axles are not adjustable you can still get some adjustment of your tongue weight simply by moving the winch support either forward for more weight or rearward for less weight.

Hope this helps somewhat.

PS.. looking at the last picture, it looks like your rear axle is almost even with the end of your trailer. That's a ton too much tongue weight. Move those axles forward.
Also, is the "lower support" you mentioned the bottom V roller on your winch?