A couple of things to maybe make it easier to just two people with one not the best sailor. First get at least a 35' mono,IMHO anything smaller starts to get a little crowded. Next take the stress out of raising the sail, raise the main by yourself while still on the mooring and leave at least one reef in the sail. Its much easier to shake out a reef than to try to put one in. As for picking up a mooring,if it really becomes an issue, again do it yourself by reversing into it and picking up the pendent at the stern and with a dock line thru it walk it forward (make sure the dinghy is tied to the side of the boat out of the way). Just some thoughts. Good luck and most of all have fun.