Thank you for sharing your setup! I also have a 2017 TRD ORP with Bilstein 5100s, but mine are 1.75" front with 1" cornfed spacer in the rear. I'm keeping my stock wheels. I have been trying to decide on 275s or jumping up to 285s, but I don't really want to do a BMC. I don't mind modding the bumper/mudflaps/fender liner.
Based you your experience, it sounds like I can probably run the 285s without having to do the BMC, which is music to my ears! Of course I know that all vehicles are slightly different and my experience could be different.