I put guide post on my last boat trailer and was fairly happy with them. It’s was an 18’ Henry O CC. When I bought the Parker one of my first thoughts was to add them eventually to that trailer. Then I realized one flaw I had with them which was that when driving on and brushing/bumping them with the bow it would bounce you to much off course sometimes. When approaching the trailer, at times I may enter the rear of the trailer crabbing some to compensate for the wind etc... but know she/I will target the front keel between the front bunks which is all I need to do. As soon as I get the front on I just power up and she will straighten up the stern as she slide up the bunks. Anyway, after loading the Parker for awhile, I decided not to add them for this reason, so far so good 4 years in. If you are winching with rollers I think guides would be even more beneficial?
Oh, I’ve had buddy bearing before and not. I did have one pop off after redoing bearings. I was told that they are prone to that if you remove them and put them back on again? I don’t know if I buy that but I have a little mixed feelings on them. If you do an annual on the barrings and they have a good solid cap maybe it’s better? Tomato tomato?