(I can't tell from that picture if the bow eye is touching the roller)
Crazy, the reason you need to get the bow eye touching (snugged under) the bow roller is to help "lock" the bow in position. Without it, the bow can bounce as you go down the road (this will even happen on boats much larger than yours). If you happened to have to an emergency brake/turn/etc, it greatly helps to keep the boat in position. If there's a gap, it gives the boat a chance to gain momentum.
I've setup many, many trailers - there's always a way. From looking at your pictures, you should simply be able to slide the winch down till the roller contacts the bow eye. You mentioned you tried it, but somehow you're missing something. I probably can't be of much more help from where I am
but all I can say is that I've never (nor any of the guys I works with) been NOT able to get the two pieces touching.
As far as the weight issue, if you don't feel like tackling moving the axles or taking it back to the dealer and paying them to do it, then try moving the winch stand in front of the "A-frame". As you correctly mentioned, if your wife can stand on the platform and it raises the trailer, it's definitely way too light.