If you farm, you want a level deck trailer, around a farm they are useful for more things than hauling machines, you can haul seed totes, large water tanks for spraying, tractors, farm machinery, skid steers, trucks and dozens of things.........................and everything is close to the ground, meaning no ladders or steps to get onto the deck.
You'll also notice shortly you get to change your driveway's and make them wider and a gentler slope so you can pull in easier.
I'll second the non ground bearing trailer, have had detaches for almost 20 years, in all that time there have been a couple dozen times when a ground bearing trailer would have caused problems, keeping in mind just once is more than enough to justify and pay for a non ground bearing trailer and depending on where and when it causes problems, might pay for the entire trailer if an accident is involved or someone gets hurt, which is usually along the road somewhere with too many other idiots who have no clue your stopped or having problems or refuse to slow down even the slightest.
Now since you've never owned a detach before, I'll make this simple, no matter who tells you its fine, how cheap they are, how much you'll save, how maintenance free they are and how much lighter its is, tell whoever is telling you that to shove the pony motor up their *** and put a wet kit on the truck from day one and run a detach off a wet kit on the tractor.
As for buying a trailer for future possible machines, buy one today that hauls what you have now, it'll also give you first hand experience in what you want your next trailer to be and how you like it. Best of luck