Is it a Valley? Looks like it may be. Just asking, because I am not too far from you, and I have an old (1994'ish) Valley. I LOVE it. I will pull it any day compared to friends newer aluminum. Just FYI-I have been offered $4k for mine, by a dealer, so you know it would sell privately for more. My trailer guy wants it-he loves it too.....
I would not say the one you posted would ever hold 2 horses. It is fine for one. I would suggest sway bars and braking system, but I am a cautious one.
I didn't even think of ask what bran it is lol. Does this trailer not have a breaking system? How does it stop, just from the truck stopping? Any idea how much it would cost to add a breaking system?
I agree with Franknbeans - 5 feet wide might be too narrow for both horses to fit comfortably; for very very short rides it might be okay especially if they both load and travel like angels. Their widest parts would be not at the same place, LOL, since one is so much taller than the other! The one thing I'd double check is whether it has electric brakes. If not, it is absolutely critical that your tow vehicle is big enough, strong enough and heavy enough to stop the trailer easily when it's loaded. Almost any truck will tow this trailer but stopping is the dangerous part if the truck is too light or the trailer doesn't have brakes.
My mare isn't exactly great about trailering, mostly it's loading she's bad for, but we can work on that, it's pretty impossible to practice trailer loading without a trailer. Once she is in she is pretty good tho, My moms appy hasn't been trailered since we bought him, his only issue was he paws every time the trailer would stop, such as at a red light lol. He loaded great tho.
Like I said thp, it's really mostly for my mare so if they won't both fit it's no biggie, my mare needs to get out and get exposure.
Although, there is the next problem, I don't have a truck lol, my mom has 2, a brand her ford F150 supercab(i think, it's got the full sized back seat) and then she's got the plow truck, which is an old 95 silverado, which can barley make it up hills as it is, I doubt it would make it up anything with a horse trailer lol. I know my moms not going to let me drive her truck everytime I want to take my mare somewhere lol, but I figure I can always save up for a truck tho, they are easy to find, reasonably priced trailers are not so readily available. Not to mention, I've never pulled a trailer