I have experience with all 3 organizations, USCCA, AOR, and ACLDN.
I've been to the USCCA conference and talked to President Tim Schmidt for a bit. He seems more like a businessman and spokesman, and I was not impressed by his 2A knowledge depth and ability to connect with the members. I used USCCA insurance for a year and found their online lessons are excellent for the average person and they have very good insurance coverage, though at a high price. I know their training counselor and their firearms training programs are a bit better than NRA.
I haven't used AOR, but know their team pretty well from outreach work, coordination with HIFICO, and other events. They seem to be good guys but are focused on pushing their products heavily and have a lot of flash and flair, which seems out of place in our culture in Hawaii. I don't feel their ability to connect with people. Although they are self-defense attorneys and filed a 2A lawsuit in Hawaii, they don't have the gun culture in them. Main issue with their insurance is you are forced to use their attorneys and I want that freedom to choose. They have an affiliate attorney in Hawaii but there are probably better attorneys here. Also if I get into an incident in another state, I'd probably want an attorney that lives in that state to defend me as they likely have better knowledge on local laws and resources, and have relationships in the local legal system. The plans are more expensive than USCCA.
I've taken a classes with a lot of the leadership of ACLDN...Masaad Ayoob, Marty Hayes, Tom GIvens, Dennis Tueller, and Karl Rehn. They are also the top experts in civilian self-defense and firearms training fields. They live and breathe that stuff everyday for decades. I really feel that deep dedication to their students, community, and the 2A when I'm around them. That is the main reason I decided to stick with ACLDN for my insurance and the low price helps too. Their online lessons are very good, a bit better content than USCCA but without the flash.