i know 2 ways to do #1. first (with the trailer coupled) is to slide the mast back and fore till its in perfect alignment, then pull the mast down with one hand and insert the pin with the other. doable but can be frustrating. option 2 uncouple the trailer so the load is off the mast, boat and trailer resting on the transoms. then its easier to move the mast ack and forth and hook up the pin. then put the trailer back on the car's hitch so you can do my above routine. as for the steps, i use whatever blocks are available at my club. if i had to do this routine often i would get a set of kitchen style folding steps. yes i walk the mast all the way up from the back forward. shoulder the mast before you go up the steps. press the mast over your head at the back of the tramp where its more stable and less leverage on you from the mast. then walk it forward.