a few things to check: at the point where you feel resistance, can you still pull the hose up and down? if so then you know that the hose itself isn't bottomed out. did you have to use a wrench all the way when you took the hose off or were you able to use your fingers at some point to loosen the fitting? PS hoses can be tricky, not just on Cruisers. look carefully at the male threads on the hose fitting and the female threads on the box itself. if you see no signs of cross threading, then you should be fine. when i did mine, i looked through the wheel well with my eyes at eye level with the box to make sure i was going in square. ( you may want to also use a mirror to get a 360 degree view around the fitting.)
if it looks like you're going in square, here's where a little faith and some experience helps. after a while, you'll develop a "feel" for when you're crossthreading something. at some point, after visually making sure you're going in sqaure, you may have to grab that wrench and start turning. if all goes well the hose will seat and you're done. if you end up cross threading it, at least you'll know what it feels like when you're cross threading something vs. something just being tight.
good luck