When we bought our first boat, we bought in October and we had a GREAT first couple of trips out. Got the sails up, engine started/stopped/started again fine, everything went really well. I was actually stoked for the next season.
The next season we moved her to a different marina near Ocean City, NJ. I had her trailered (wasn't sure I trusted the outboard yet) and had to have her dropped in at a different marina because our "new" marina didn't have a lift that could handle us. I went down to the boat the day she was launched (bad weather the day of the trailering pushed back the launch), and started talking to the guy that ran that marina. Turned out, he's a very accomplished racer with lots of neat stories. We talked sailing for easily an hour. Then I packed up my stuff, put the engine on, and got everything going. I set out, followed the GPS and maps, everything was going good. I wended my way through the back channels and caught sight of our marina. I called my father-in-law and told him he could leave his place to come pick me up (allowing for his drive time). Then I ran aground not more than 100 yards from the marina. I cut the turn into the marina too tight, and the outgoing tide made things very shallow. I could have walked to the marina (literally). It was so shallow, TowBoatUS couldn't get TO me to get me off. My father-in-law left to get lunch, and I sat there for about 4 hours putting on the sails and doing a bunch of other random stuff. When I could finally float off, I managed to get into the slip by myself (lines hadn't been pre-rigged or anything) and tied off.
That was the first "bad" thing to happen. Add in engine problems (water pump didn't want to pump, and the "replacement" engine that we bought died, twice), running aground one other time, and then (on the new boat) catching the jib sheets in the prop, and more engine problems (damping plate let go on the new boat), and I guess I can see why my father-in-law still won't go out with us!
But, I look at it like BLJ said...nobody got hurt, no major damage was done (especially to other people's property/boats), so it was a successful day. Sounds like you learned a lot of good lessons.
Wait 'til you single-hand her.