My point is that NEC is sometimes over eager because it deals with extremes. If you take it as gospel, you’ll have a hard time finding approval for every situation.
Do I think your setup is safe? Absolutely.
Are you in explicit compliance with NEC? No, as per code you should run a protected conduit…
National Electrical Code (NEC) does not allow extension cords in lieu of permanent wiring (NEC 400.8(1) – 2014 Version).General rule– if equipment is powered from an extension cord for more than 30 days, permanent solutions should be installed.
You’ve essentially made a DIY extension cord between the outdoor receptacle and the enclosed outlet. At least now you know why Rachio cannot sell / advertise this feature.
Your old setup was different because the cable you’ve repurposed was hardwired to the transformer, it was not considered an extension cord, thus didn’t fall under the same rules.
You’d be more to code if you were to plug the Rachio’s transformer right to the outlet and had the low voltage AC going to the unit. Would it be more prone to damage than what you have? Absolutely. Did you choose the best long term option? I think so. Are you technically in violation with NEC? Yes, I hope you are ok with that.