The one you're calling #2 jumps out at me, for several reasons. First is something I'd have to verify in person, and that's that it's as solidly maintained as it looks. From the seller's pics (which, ya gotta remember, almost always are of the object's best features
) I don't see any glaring flaws.
I do like that it appears to be a 5x8 bed with the wheels tracking outside the bed. Yeah you'll have to design around fenders but that's not so bad either, it does give you the option of going to six by eight with five of it flat floor.
I do like that it appears to have decent wood, not rotten or beat up, implying that at least a hint of care was shown to the thing's upkeep. The fact that it's unpainted is immaterial. Paint sometimes is its own worst enemy in that it traps/hides problems. (Green one could be a flaky mess held together with the paint
)
Take a jack with you if you have more than 10-15 miles to get it home and pick up each side and roll the tire. Push it in and out while you're turning it. Should roll smoothly. If it's sloppy but smooth rotating, probably be fine to take home to do the maintenance on it. Additionally, it'll be a GOOD indication of how much use or how little maintenance it's gotten. While you're down there, take your handy little pocket tape measure and measure the wheel lug bolt pattern. Looks like it'd be 4.5" but can't see if there's 4 or 5 lugs. Either one is readily available as a tire/wheel assembly from most anywhere like Walmart, Tractor Supply, HF etc. What I'm saying is really, so long as it's not an oddball metric of some sort it's not a cause for concern since they're (the wheels and tires) all over-built for a lightweight trailer.
The price is a big plus. I don't know about your state, but here, $300 is just about a minimum to break even buying .vs. building yourself from scratch with found materials and getting lights and plates on it. Basically, all used trailers are 300.00 trailers with varying amounts of extras.
All said, at least do go look at that #2 you listed, and when you do check the coupler, tongue, suspension and axle for leprosy. Not sure how bad rust is where you are, or more to the point where that trailer's been!
Surface rust not so bad, it's on everything ferrous here. Deep pitted candidates for a leper colony, are things to beware of. If the coupler and tongue are free of scary looking rust and the rest doesn't scare you off, show the seller a couple hundred and start from there. It's already established the seller's gonna go down, looking at how he accepted FB auto-adjusting the price over time.
To counter your cons, if you do get this one, you've got a couple hundred dollars to play with as far as A braces for the tongue, sawzall blade or torch gas to remove the sides, things like that.
Bottom line is, it'd have to UN-sell itself in person, to me. Good luck with your hunt!