Been towing heavy things on farms 40+ years so here's hard won wisdom...
Go to Tractordata website to get the weight of
L4701 plus front end loader if applicable. Add loaded tire factor (messicks has a good page with tire size and weights of typical fluids). Add diesel capacity, other margin for accessories on the
L4701 plus chains, chain binders on each corner of the machine plus straps on EACH attachment. This is your load weight requirement. Add your weight of trailer and Add hitch to this separate number. Subtract both numbers from Ford's Max Trailer Load number and ensure you have no less than 10% safety margin left (preferably more because sooner or later you'll tow with a load in the truck bed or more gear than you think).
My gut says you get either an 18' or better 20' 10K gross lbs tandem-axle trailer with brakes on BOTH axles and battery backed break away safety brake that recharges via the 7-pin light + brake controller connector to your truck... weighs around 2300 to 3000 lbs empty depending on quality of trailer construction which means you net to 7000+ lbs for the tractor and the goodies above maximum. But you will be smart and not max it out and always leave safety margin (for God forbids like truck brake wear, hot days if the brakes or tranny starts to overheat below Ford's "max" rating numbers, etc.). Once you have a good trailer, life becomes a lot simpler for property maintenance and friends seem to come out of the woodwork asking for favors so be prepared.
Get a drop arm and ball rated for the trailer above. These are rated for 5K, 7K or 10K gross typically. A 10K trailer takes a solid shank 2" drop arm and at least a 2 5/16" ball that's heat treated to cover 10K lbs. Spend the money on this. You're not worried about the vertical tonge weight, you're buying the strength laterally to stop or pull that 10K lbs horizontally here. And check the hitch capacity on the F150 while at it (if it's an after market hitch, this is critical to check, but you may have a factory setup to support 10Klbs already.) Remember, the truck will squat a couple or more inches with the tractor and trailer, so an adjustable drop arm typically on a anti-sway hitch kit is a nice thing to have to adjust the height of the ball here.
Get a trailer braker controller NO MATTER WHAT ANYONE ELSE SAYS. Tekonsha Prodigy is good. Curt models with better displays are good. Make sure the display is clear in direct sunlight as you have to adjust trailer brakes for either "empty" or "loaded" conditions (brakes will lock on an empty trailer if brakes not adjusted down for example.) If the Ford has a controller already, good. If not, get the controller installed or buy the adapter yourself as works best. Usually, the higher the truck trim level, the easier this step is.
If you do anything trips with this rig on highway, get an anti-sway hitch with the anti-sway bars that connect to the hitch ball. It's key for highway trips in wind, 18-wheeler drafts, etc. to avoid trailer swaying, then loss of straightline control. And it's a blessing if you ever have a real emergency stop to keep the truck and trailer better aligned as each trailer wheel, brake and truck wheel + brakes all interact to stop at varying little bits.
Do test drive the trailer empty including backing up and the new binders and chain setups before you get the tractor loaded. It's goofy to do, but it pays off.
When using binders and chains on a tractor, remember the top risk is the tractor sliding forward on quick stops. Ensure the rear binders and angle pull the load to the rear and the front binders pull forward of their contact points on the tractor. If done properly, all 4 tires "squat" once you've tightened her down as well.
Your F150 w/10K+ gross towing capacity will pull the above setup like a champ with the above covered. FWIW, I tow right near the limit on a 6cyl Honda Ridgeline with AWD for my 2025R, loader and 1 or 2 attachments. But I invested in the above and the truck pulls and stops quick and straight. All this sounds more daunting than it is and enjoy learning the tricks of the trade. Then you can share with someone else some day.
