The best trailers for the price IMO are not national brands, but small regional brands from local fabrication shops. Surely there's a trailer dealer or two near you? At least take a look; the price comparison for what you get might surprise you. I'd rather have an over-built trailer than an under-built one. Remember, the big box store chains negotiate down to the penny on supply contracts. Local dealers are more concerned with quality.
Not always. I have a friend that bought a 16' dump with 4' side walls. Worse welding and design I have ever saw. The lugs the hydraulic cylinders connected to under the bed ripped off like a sardine can top rolling back. No penetration on the weld. Of course it was only notice when I borrowed it. So I cut all ther original junk out redesigned and wielded the new in. There will never be a problem with it again.
1.5 hrs each way to mow 3 round trip + mowing time? I think I would just pay for a lawn service in here area to mow it for me. It would be cheaper.