Depending, a running of the mill double axe trailer might not be enough. Cheaper trailers usually have 3,500lbs rated axles, giving you a capacity of just over 7,000lbs (ignoring a couple hundred lbs of hitch weight). The trailer itself will probably weigh 2,000lbs, leaving you with 5,000lbs for tractor & implements. Probably enough, but it depends on the tractor & implements.
Remember, a longer trailer gives you more room to balance the load so you get proper hitch weight.
I towed my
L3200 (with loader), back blade & rotary cutter home behind my 2009 Toyota Tacoma, which has a 6,000lbs tow rating (I was close or just over) Brakes, suspension & power (in order of importance) were all tapped out, but it was fine for a half hour backroads trip. But I now have a beater F250 for future hauling needs as I don't want to beat up my Tacoma.
Hauling, maneuverability & tearing up the lawn are the only real drivers to get a small tractor. A bigger tractor will be capable of a lot more. I'm guessing 75% of the time or more I've seen people talk about improperly sized tractors here on TBN they want a bigger one not a smaller one.