Well, it's probably an OK winch post. I'm probably wrong in my post. When I first viewed his traliers design it appeared that the winch post base would have to be real wide to fit closer to the hitch ball. Now that I see the beam underneath those top two aluminum curving plates that one could actually drill holes for placement of the U-bolts. I orginally feared the OP might think he could just bolt the winch post onto those top plates.
Drilling new holes without first getting the rig with proper weight on the ball is not going to be easy on this "one trailer fits all boats we sell design" This sales shop should never have allowed his rig to be driven off their lot hanging off like that no matter how excited the owner was to drive it out . . again, in my opinion only because when I bought my rig new they pulled the same thing on me just dropping the boat on the trailer. It took me many tweaks getting mine correct. Almost every aspect of matching my trailer to the boat was wrong.
I had awful tongue weight which was causing the rig to bounce all over the place when trailering and it would sway back and forth at 55 mph wearing tires down.
My rig was hanging a foot off the bunks, which as another poster has said would have caused hooking to the transom.
I had to move the axle back one or two sets of holes after getting the boat in the right place. One should not have to "add" bunk pieces for a boat that is improperly positioned on the trailer. Bunks themselves can be repositioned.
I had to do all this stuff myself as I took delivery in June and to bring it back to the same enept people that didn't have a clue (or did not care and are now of course out of business) I was not going to give them the boat as July and August which were also their busiest months.
Re-positioning the rig yourself in your driveway is sometimes not easy as the bunks are are dry. I first had to slide the boat onto my lawn to reposition the axle 1 hole. Which of course was not enough. After a test drive I knew one hole was not enough so this time around I brought it down to a quiet boat launch and floated the boat and moved the axle in the parking lot for the 2nd hole.
Most important is getting that tongue weight correct first before you pull out the drill

If you have to re-position that winch you are going to have extra sets of holes, more holes only serve to weaken the overall structure.
Moving boat up is easy since you have a winch, but in your case your winch is not going to be bolted down yet. Getting rig off trailer is a pain as is moving it backwards on trailer. I had to use a chain hooked to the rear tie down hooks and around a tree to get boat of and my rig empty is only 700 lbs but the O/B is like another 150. So unless you have jacks, pieces of wood, jack stands it's a tricky process moving that kind of weight around.
Take a pic for us of the area behind your wheels to see if there are extra axle holes or it's just clamped on. I had 4 sets of holes.
None of this is really your job to do when you buy a new boat, it was the dealers. But if you don't want to lose it during boating season if you take pics along the way and since there are so many variables here you might have to deal with: bunk position, post position, boat position and axle position we can help you along the way. I only have experience with my own last few rigs as to trailer positioning and I never knew how off it was until other posters chimed in seeing how my rig was positioned incorrectly.
There are a lot of posters with much experience here (not me). They will chime in and help you along the way if they see you are moving in the wrong direction tweaking your rig. They are usually the ones with many thousands of posts, I personally tend to rely on their input first before I'd pull out the drill!
If you pull off the post first, reposition the boat and maybe tape the post farther up and then put a bathroom scale under the end of the tougue under the hitchball lock with a board across the scale to rest the trailer end on and see if you can get it around 10% to start. Some setups might need 10-15%.
others 7-10%. This is a link to "my" trailers webpage:
http://www.shorelandr.com/pages/pf_trstep3.htm
Google this for your trailer. See if they have it up on their site or look in your docuementation if it came with any.
The only way I knew I had the correct weight was trial and error test driving. You are not going to have the liberty of moving the boat up or back a few inches once that post is mounted do to the design. Most trailers can be properly fitted to a boat, but most dealers are not going to take the time to do it.
Note: again, I'm no expert but if it was my rig, since you may be repositioning stuff, I don't like the way the right bunk is not sitting on a flat part of the hull. Maybe its OK? but I'd reposition it to ride on a flat part for "my" boat if I could, unless you don't plan to trailer much. I sometimes travel 2 hours back and forth for just a day trip depending on which lake is less windy or rainy that day.