I owned a roller with my Maycraft 25 and now have a bunk with my Judge 27.
The roller trailer gave me access to more shallow or short ramps since you dont have dunk the trailer as much. The bunk is quicker and easier on nice ramps as I can quickly powerload. Maryland state parks have about the best ramps I have seen so I prefer my currernt bunk. (but I also cannot use one of the ramps I used to use in NJ with my roller trailer). I do have polyslicks on my bunks so sliding on and off is a breeze.
I currently have a Venture trailer. They are not top of the line but it came with my boat. I have had a lot on it rebuilt. I have converted to Kodiak stainless brakes, upgraded my tires to goodyear radials, and will be having all the hardware redone next year.
When shopping I would recommend looking for a torsion axle trailer (sits lower), disk brakes (kodiak if available), stainless hardware, and radial tires. LED lighting would be nice too. I personally prefer galvanized steel over aluminum trailers but that is just me (less flex but heavier, not as pretty either).