I ran ny R27/OB solo most of the time.
Remember that docking is not a race. It's OK to back out of the docking maneuver and retry.... several times if necessary to get it right.
Practice is the best way to get comfortable with the docking with the outboard. On my outboard I placed a red tape down the center line of the outboard's casing, and this visually indicated which way the outboard was oriented. It's easy to get a bit confused in tricky docking situation (especially with a nasty beam wind moving the boat in unwanted directions), and the red line always gave me immediate clues on the engine's angle.
If dock in a wind, alway try docking on the windward side as this will allow the boat to be pushed up to the dock side. Docking on the lee side can be a bugger, even with the very powerful 300 HP motor.
It's alway good to point the bow at the dock side, and as you get close use the motor to kick the stern over to straighten up the boat. However, if you docking on the lee side with a strong wind the R27 will move very quickly away from the dock and not give you too much time to run from the helm to the cockpit and then onto the dock with a line in hand. I've had this issue several times and have had to organize my line to be attached to a mid cleat so I can at least get the boat back to the dock side without the bow hanging out in the fairway too far and being unable to get the boat somewhat lined up to the dock side.
If there are other boaters about and you're having trouble docking in windy conditions, they are more than likely to come to your aid.
The hardest part of docking is when trying to get into a small space between two other boats. It's kind of like parallel parking a car between to other cars.
Again, docking is not a race, take your time, back away if necessary and try again, even seasoned boaters make mistakes, other boaters may come to your rescue, and practice as best you can in your marina. I found the early mornings when my marina's fuel dock was empty and being alongside the guest docks that can be empty at times, makes a good space to practice, especial with no wind to complicate things. Remember, when the stern moves one way, the bow will move in the opposite direction 😉 .
Oh, and yes the bow thruster is really quite useless in windy or strong currents, unless the waters are calm, no current and no wind. Do not rely on the bow thruster too much. Just a slight wind on the boat's beam places quite a side force on the boat, and with the R27's flattish bottom it will move sideways quickly. I cannot count the number of times I've got alongside the dock, then running out to the cockpit only to find the boat has moved off several feet from the dock side... it can be a bugger at times when being solo.