After 3 trips to Home Depot (good thing we live really close) I finally got the right connection for the pressure washer to make it work. I'm not sure why the hose-to-machine connection had to be so specific, but glad I could finally make water come out of it.
Well....the stubborn paint still didn't want to let go. When the paint stayed there and the wood around it started to splinter up I decided it was time to scratch the pressure washer off of my list of options. So with day 5 approaching and problems still looming I did what any self-sufficient person would do.
I looked up a handyman service online to do it for me.