The outboard vs inboard argument comes down mostly to when, where, and how long. Besides the reasons why it makes a lot of sense for boat builders to go with outboards, they (outboards) are certainly popular as an option for a number of reasons. If you want/need to get somewhere in a hurry they sure can sprint with the amount of HP that can be bolted on, but they don't do all that well anywhere in the slow to mid range speeds so your maximum range is limited. An Inboard single diesel can just keep on going and going while sipping fuel resulting in some extraordinary range capability though top end is not exactly screaming fast by any means. Outboard parts and service are usually more available and certainly cheaper than a diesel inboard, however if putting a ton of hours on the engine(s) and properly maintaining them the diesel could outlive 3 or even 4 sets of outboard motors. The key there is maintenance, as diesels can be very temperamental if not maintained properly whereas the outboards can be abused pretty hard and still live up to their expected hours (lifespan).
So if you're planning on traveling long distances, going out in less than favorable conditions requiring a slower pace, and have more time to dedicate to the vessel then the inboard diesel should be the way to go. However, if you're in a hurry and only have that one day or two off to use the boat, and need to run out and back at speed... Outboards are certainly your friend. Same goes for trailering as there is far less to procedure and care needed vs with the diesel.
I don't have a command bridge, but certainly wish I did sometimes... Not very often though. In my case I have a substantially low bridge to clear between the slip and harbor mouth (8' clearance at high tide, 14' at low tide) so the extra height would just make for more work lowering/raising everything along with even further limiting my departure/return windows. Another factor that can come into play is the effectiveness of the solar panel on the CB as there are so many additional shade structures and much less space for expansion of the array. Without the CB additional panels can be added with ease for charging capabilities in excess of 400-800W depending on layout.
Docking alone really just boils down to one's proficiency with running a single screw (unless you have outboards and/or a joystick). Without even touching the thrusters it's pretty easy to spin the vessel in hardly more than it's own length (depending on the current since it has a nearly full keel that gets pushed around but the thrusters can compensate when needed).
In general loss of the power plant will leave you stranded waiting for seatow or vessel assist as you eluded to. Having a kicker can be a good alternative, but the biggest issue there is range since it'll be operating at full tilt to make decent headway and the auxillary gas tank may not have enough reserve to get you far enough back to refuge. While not a perfect solution, I carry onboard an electric outboard for my inflatable tender which can be mounted to the swim platform and used to make way at a slow but steady pace of roughly 2.6 kts in practice. What is convenient though is the ability for it to charge while underway plugged into an outlet in the cockpit. So if there's sun the solar keeps up with it virtually indefinitely, and as long as the generator still works the remaining diesel can be used to supply power overnight or during less than optional conditions. (Assuming the fuel tank isn't the problem)
