Couple things come to mind here.  If the stern of the boat is floating around too much, you probably still have the trailer too far in the water.  Dip the trailer in and get the bunks wet, then pull back up until the front 6-8” of the front bunks are out of the water.  The 23LSV isn’t a small boat and depending on the angle of the ramp, you may have to winch further up than you expect.  That may be made difficult if you have the low capacity winch on your trailer.  My 2008 is nothing like your boat, but I did upgrade to a 3200lb Fulton F2 winch this spring and let me tell you, it was worth every penny.  
 

Oh, and this group loves pics. So please show us what your boat looks like!

My 2001 malibu responce oil gauge stop working, the oil pump is fine, so far I replace the oil pressure sending unit to the dash and still does not work. Could it be the oil pressure switch to the ecm?? Or what else could it be, there is power to the gauge cluster.

Ok, we are new to this type of boat, but we really seem to be struggling with getting it back in the trailer after a day at the lake. We have watched a few guys with classics who trailer their boats on the first try no problems… We learned we had the skids to far in the water… the stern was floating around and couldn't get the ratchet tight enough. Now we just seem to have trouble with the boat being crooked, resting on or near the foam covered pylons and then having to pop the boat back off the trailer to try and get it straight!!! Super frustrating and asking for any tips/tricks?

2017 LSV

Thanks in Advance! 

Yes to both, it seems like by bleeding the air off the fat sacs we created a reverse siphon. We can fill it. Make about three runs at 1-2 mins each with new surfers and it’s about 70% full.  It’s just the one side… 

See that. Not sure. I am wondering if you need that shim kit. Don't have a pic but someone here may chime in.