To anyone curious how the trip turned out, I ended up making it only with my fiance. Scott offered to help, but then I was suppose to have a friend to help -- that fell through last minute. Some lessons learned:
1. Use the channel in Middle River I say this for two reasons. First, there are crab pots spread out all around Hart-Miller island and it's like sailing through a mine-field. People said to watch out for crab pots, but if you're new you really have no idea how bad it can be. Second, we missed the turn to take the channel south of Hart-Miller so we added some time to our trip. If we were in the channel, I'd have followed the markers better.
2. I learned why sailors hate power boaters. Maybe that isn't universally true, but after having innumerable power boats zoom past me at break-neck speeds, I don't care for them much. I understand the appeal of going fast on the water and love to jet ski (though it's been a long time). The problem is that most of them weren't considerate of the effects they had on others.
3. The approach to Baltimore was rough. There were 10 knot winds predicted for the day from the NW. Right around the time I started approaching the key bridge, the winds seemed to spike (from a couple miles out). That was miserable. We couldn't tack back and forth handily enough to make sailing worth while. So we dropped the sails. With the strong head wind it was still rough. Also, I left the jib attached but tied it in a bundle. That was a mistake. With such strong winds it flew up and caused problems. I'm not sure what the right approach is to lower the jib on a small boat in rough weather. I ended up squeezing through the air vent/portal (?) on the deck and crawling up to pull it in. I'm sure it was a sight.
4. I'm going to go with Baltimore is a good place to learn to sail. I don't think the rivers are meant for sailing. I see people doing it, but you need to know the area really well. Out further into the bay was rough in a small boat. The harbor is busy but no one is speeding along. Most of the boaters are respectful and the waters are placid. There are down sides to that I'm sure, but for us right now the harbor is nice.
5. The VHF is mandatory. We only used ours to hail the marina, listen to the weather, and coast guard reports. It felt reassuring to have it and I felt it was a safety line that let us keep going when times were rough.
6. To sailors, don't abuse the rules of the waters. I had a sailboat beat back and forth across my bow over and over. I couldn't have sailed the course that they were, so I know avoiding me wasn't a high priority. But after I've diverted 3+ times for you, please show a little courtesy to boats under power. (yes, I hope to remember this while I'm under sail)
If someone could provide feed back it would be appreciated. In particular, I'd like to know the best procedure for taking the jib down in at least somewhat rough weather. I'd also like to know if there's a simple trick to fix a small outboard motor to not turn. It seems to flip over at the most in opportune moments, so any thoughts on that?
Thanks again everyone for all the advice.