I have cursed these RT fittings ever since they started requiring them. Standard compression fittings we used before were just fine. When used outdoors you will get more water inside the raceway from condensation than they will ever leak. Outside of direct spray or diversion, probably get more water inside from condensation than a set screw would leak in a moderate rain in most cases also.
Haven't seen any that are easy to assemble. Most the end of tubing hangs up on the nylon sealing ferrule and you have to completely dissassemble it to get it to go together properly.
With the connectors, I was taught to thread them into a myers hub on drilled entries into enclosures (above live parts anyway). When RT became required I figured that rubber washer was supposed to be the seal, so I started using without the myers hubs. It was only about a year after install I came back to a project or two where I did this and noticed the rubber washer was deteriorated enough it didn't seal well at all, or even was completely gone in some instances, leaving a bigger gap (and definitely no good bonding) at the entry point that would likely let more water into the enclosure than if I had used a set screw fitting from the start.
I now throw those rubber washers away and have gone back to using a myers hub for those sort of applications. No they are not listed for that, yes they work better in the long run than what is listed for the purpose.