To followup with what Jim posted
Fishing - The R-278/OB is well equipped for this type activity. Plenty of cockpit space, features inside cockpit for the fisherman, down rigger plates, electrical for the down riggers, extra ice Fridg in cockpit, dry well in transom. Boat will get you to your fishing ground quickly.
Day trips... R-27/OB is well equipped for day trips, has the creature comforts things and is fun to drive.
Weekend trips... Nice spacious V-berth, well appointed head with shower, propane stove/oven combo, Microwave, coffee maker, TV with DVD player, Fusion radio music with 6x speakers, Bluetooth connection, USB connection, 5 120v outlets, Electric grill in transom, huge storage space all around.
Great Loop.... all of the above facilities on hand, OB is quiet at low speeds, fuel efficient, no diesel smells...
Open sea.... Boat runs well and deals with things better than you can handle it.
Overall, very good value for the money and GREAT Customer service for years to come.... and you have this forum to help you along with all your concerns/questions and advice.
N.B. Your requirements for boats and boating today are one thing but as many people can tell you, the requirements can change over time so give that some thought to this as well as for the immediate moment. The future to a large extent is unknown, but think about it anyway.