I don't know of a right or wrong for this discussion, but after working at different dealerships and with different manufactures products here is what I have observed. Pretty much no boat will winch up easily, unless you back the trailer in far enough to completely wet the bunks first. There are some ramps that if you do that you have the famous "guys lifting the trailer underwater while the drive pulls it out because your wheels fell off the end of the ramp show". Driving the boat onto the trailer is the easiest, and if the bunks are wet, will usually work with minimal throttle (after enough practice you can hit the trailer with enough speed to accomplish this also, without damage). It is easier to center the boat if it has some type of side guides, again with practice they won't be needed except for helping center the boat on a tilting ramp. I prefer the taller pipe style posts at the rear of the trailer, they usually stick up far enough on any ramp. The side board style will do a better job centering while pulling out, but on a steep ramp I have seen boats up on top of these also as they are usually only slightly higher than the fenders (the pictures of the American Skier style look to be a better setup than most). The Nautique style trailer is a similar trailer to the American Skier. The difference is they use a nose block that you drive the bow of the boat into. Definitely the easiest, but here are the downfalls. The bow of the boat will rise a little as it is pulled out of the water and if you are too "tight" against that block it will scuff the rubrail (which is why it is called a rubrail, but I like them undamaged). You also can't put a mooring cover that "hooks" under the rubrail. Both of these were not really issues with me, experience on how tight to be in the nose block will solve that one, and my boat is kept in a garage and doesn't need a mooring cover while on the trailer. The main problem with this trailer is it will flex because there is no support under the bow which allows the boat to "bob". If you are tight against the nose block, it will peel and scuff the rubrail. My preference is the Nautique style, but the American Skier style with the support under bow I think would ride a little smoother, and I haven't owned a Nautique one long enough to see if the constant flexing of the trailer causes damage to the frame, or for that matter the boat. I think this is a pick the lesser evil that works best with how and where you boat.