I think 2 motors is a fine idea. But whether you do that or not, you need to get some grease on the leadscrews, or it is just a matter of time before a leg seizes up on you.
Most trailers don't have zerks, and if they do it will only be for the bevel gears at the top. The leadscrews cannot be lubed through a zerk, unless you just willy nilly fill the leg with grease. You need to get the grease into the follower nut and along the threads of the screw.
I drilled access holes in each leg, and I use spray grease with a straw nozzle to direct the lube on the screw. I use motorcycle chain and cable spray, because it is very clingy, but regular old grease will work too. Heavy stuff preferably. You can see where I drilled the holes in the photos below. They are only about 3/8" diameter.
Once you lube the leadscrews (they are NOT worm gears BTW), I think you will be pleasantly surprised at how much easier your motor handles the load.