I didn't add any switches on my tractor. However, I have looked into adding some more on my Ranger. Companies make nice panels to hold rocker switches. I would do something like this one. It would be also an opportunity to add other types of connectors like USB etc.
I have an L2501 HST with R4 loaded tires. I thought I didn't need chains until I almost slid off my gravel road. That could have been bad since it had quite a slope off the road for drainage. I suggest putting chains on even if you go with ladder chains like I did.
I don't use dollies for attachments, but I take off the castors and put them on other frames. The dollies are pretty cheap on sale. Otherwise, I think they are too short for most furniture.
I put attachments on pallets.
I wouldn't put rye on it. I'd restore with native grasses although the fish and wildlife or agronomist in your seed supplier are both good choices as well as the local farm extension agent.
Congrats, nice tractor. I’d buy an implement for the weight on back. I do road maintenance, and so I’m partial to a rear land plane. You might be better off with a rear blade or box blade.
I think I'd try a flail mower with hammers or disc attachment. I'd use a land plane after instead of a box blade. The difference is that a land plane will automatically drop the soil.
Do mow it short before you disc if that's what you will try.