I believe that the 285's are about the same size as 33's. Even 33's aren't 33 inches tall most of the time. They should be safe even with some flexing. As far as I can tell, the Pintlers have more backspacing (they position the tire closer to the frame) than most aftermarket wheels. 4.5 is ideal and those have 5.2, I think. Maybe someone with Pintlers and 33's will chime in.
You could run the 305's but you might rub when flexed but you could run 35's with properly backspaced wheels on the street and mild trails with no issue. If you're wanting to get rid of the rake but not get much lift, try a leveling kit. Teraflex and Rancho both have good kits that won't affect geometry enough to worry about.
Wait, you have a 2015 Wrangler?