Rough first sailing experience !!!! Sent by a friend

So I purchased my first sailboat this winter (vanguard nomad). I took some sailing lessons the past 3 summers and was very excited to get out on the water. Things, however, did not go well. I have to motor about 1/2 mile with my mast down to get past 2 low bridges. On my first sail I did this without removing the boom. I found out a bit late that this put too much pressure on the gooseneck and sheered the bolts off of it. First sail ended before it really began! I was able to repair the gooseneck on my own. Which I was very proud of because I know that mechanical failures are part of boat ownership and I need to be self sufficient. So now it was time for my second attempt. I made it under the bridges and was getting the sails set up when I realized we were drifting a bit close to shore. No problem I thought I will just start my little 2hp engine and motor away. It refused to start, we drifted into a dock and bumped into a ski boat on boat lift (slight scratches to my boat no damage to said ski boat but I still left a note for the owner). I managed to get off of the boat and pull us over to a vacant dock at which time my son got off and held the boat while I checked the engine and finished rigging. I managed to revive the engine and pull away from the dock. Good to go I thought, I went to drop the kick up rudder and the wire snapped. I didn't realize at the time how important that part can be. Because of the lack of real steering sailing was impossible. I quickly became frustrated and headed for home. I have repaired the rudder, but I am now leery about sailing. I have learned a lot about my boat, but it has caused me lots of stress instead of being the fun and relaxing hobby I hoped it would be. Oh well, I have a few more tries in me before I look for a boat for sail sign. Here's hoping for improving fortunes.