Thanks! My state is 4' as well. The times I will need to haul the tractor, FEL, and brush hog will be rare. This is the only property that I maintain. I primarily bought the trailer for other tasks, but wanted to be sure IF I needed to haul it I could safely and legally. I've still got some room at the front to play with. I was trying to be generous with how much room the bucket will need as I've ordered the Piranha toothbar.
You are in great shape. Far better than 90% of those hauling tractors around the country. My TPMS is eyeballs on pavement, looking down the tire vertically, with load on the trailer. The photos are excellent. I think you're really just showing off nice equipment (and that is good too.)
Very pertinent to find that you are only hauling the load as shown fairly infrequently & just making sure you are OK doing it. You are.
Back to your orig request for experience:
1) I've used an 18' trailer very similar to yours hauling a JD 4800 not all that much different than your
L2501, little bigger. With a 6ft bush hog and a loader. Brakes on one of the two axles. No problems. I often put the bucket forward of the front rail a little. Rest it on something like a timber scrap and tie it down. Depends entirely on what you need to do to get reasonable tongue weight.
2) Tongue weight: I usually drive the load forward until I get a 5" drop in the hitch at the hitch ball. [Context is 4wd std full-size pickup truck] You will be fine that way especially if not doing all that much hauling in this configuration. I got a neat gadget 3 Xmas ago called a ____ (forgot) and now the app is "Better Weigh." It plugs into your truck wiring harness where the diagnostic plug normally taps in. Incredible amount of info can be had this way including overall weight, tongue weight, payload, etc. That works because of F=MA in physics and that your truck has built in accelerometers. Requires a short acceleration run to get the data. Fun to try. Works. Readout is on your smartphone. Around $90 I think but mine was a Xmas gift.
3) To the smaller side I use a 14' single axle trailer (but heavy made one, 7,000lb axle, bigger tires, etc.) on which I just hauled a Kubota
B2150 from Iowa to WV -- sweet and smooth. No hog and no loader. No brakes on trailer.
4) To the larger side, I use a Pequea 21ft deck-over to haul a larger MF2660. It has brakes on both axles (PA law) and the hang over of the bucket and the 7ft bush hog are pretty much the same stuff as it was with the John Deere on the smaller trailer, just a little larger in all dimensions. I use the same kinds of tie down and same considerations you mentioned.
5) From all of the above my view is that you have a near-perfect, as described, tie-down. You will have zero trouble pulling it or doing your occasional towing with the load as pictured. You do need to run the load fore and aft to set your tongue weight. Tow with tractor in-gear, brakes set, etc. I say the most important chain in the tie down is the one that keeps that load from coming into the cab with you if you hit something. Usually for me that means a strong chain around the rear axle or 3pt of the tractor tied toward the back of the trailer.
You're lookin' good.