First it looks like you have wear on the inside thread all the way around the tire. That is a tracking or a negative camber problem.
Second you have a diagonal wear across the tire. On a trailer with matched tires that is usually a wheel bearing issue. But since you said you mix and match tires I would lean to that as the problem. Diagonal wear can also be aggravated by alignment problems.
Since tracking can cause both of these problems; I would be checking the alignment first.
The cupping and flat spot wear caused by out of balance; worn shocks; or braking issues; is usually straight across the tire so I do not think any of these are the problem.
To check your alignment measure from the hitch point to a axle point on each side. This can be hard to do sometimes due to under trailer interference. What you can do is mount a straight edge that is wider than the trailer across the front of the trailer. Measure from outside edges of this straight edge to the hitch point to get it perfectly straight. Then measure down the side of the trailer from the straight edge to the center of the axle.
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Today's Featured Article - New Hitches For Your Old Tractor - by Chris Pratt. For this article, we are going to make the irrational and unlikely assumption that you purchased an older tractor that is in tip top shape and needs no immediate repairs other than an oil change and a good bath. To the newcomer planning to restore the machine, this means you have everything you need for the moment (something to sit in the shop and just look at for awhile while you read the books). To the newcomer that wants to get out and use the machine for field work, you may have already hit a major roadblock. That is the dreaded "proprietary hitch". With the exception of the
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