well I think it comes down to what will you be hauling and what does it all weights
there are pro's and con's to both, pending what will be hauled on it
and keep in mind, that many states require a added credential on your drivers lic once you start towing over 9999 lbs, so are you ready to add that to your drivers lic and the added costs that come with it
as MOST deck over trailers will start at 12/14,000 lbs and go up
and deck overs have steeper loading , and higher center of gravity ,
so pending gain what your loading
most between the wheel trailers have lower deck heights, lower angles to load, and go up to about 14,000 lbs, but even these trailers in many states, require more than your standard drivers lic if you get one made to haul over 9999 lbs!
for skid steers I like the lower deck and load loading angles, when getting into larger machines, the deck overs get my vote!
but again, really the deal with trailers is getting one that can handle the weights of what you want to put on it!