I have no idea about the feasibility of the day charter market in Annapolis, so I'll leave that to others to comment.
However the fees for the necessary licenses include:
- OUPV course ~$550 (optional - but strongly recommended)
- $445 in miscellaneous costs (Physical, Drug Test, Drug test enrollment, Testing Fee, Application Fee, CPR/First Aid Certificate, etc.)
- TWIC ~$145
About $1200 in costs, plus time.