re making it easier to pin the mast base option #2 : with the boat still on the trailer, roll the boat back on the trailer just enough so when you uncouple it the trailer tilts back and the boat's transoms are touching the ground. be gentle. then rig the mast as above, the only difference is the mast will be easier to pin because the top of the mast will be on the ground and you will be able to place the mast base right onto the pin bracket, you wont have to 'lever' the mast base down to the pin bracket. if i were doing this on asphalt i would put a cushion (life jacket? rag?) under the mast tip. after you are pinned you can recouple the boat and trailer to the car and proceed. i would use a 3 step folding kitchen ladder to step up to the tramp. i also have a small winch on my trailer's mast support post, it helps keep the boat from accidentally rolling backward if the trailer is tilted, and makes loading the boat easier.