Personally, I think that a 28 foot stern drive, single motor boat is the
toughest "to control" boat out there. Anything larger, you'd almost have to
go with twin screws. Anything smaller, you could "man handle" your way
through some mistakes with the help of 2 deck mates. Just thinking about
backing into a tight slip on a windy fall day on a 28' single screw makes me
wince . .

It's easy to see why you would be wincing.

I wouldn't "back" my 36-foot, single screw boat into a tight slip on a windy
day. Not without using a spring line. Unless there's some reason to be stern-to
at the central float, more single screw boaters approach the dock like most
sailors, bow first. A head-in docking is easily accomplished with a single
screw boat in any type of conditions one would ever consider venturing out in.
(Personal worst conditions
I have ever docked my single screw, non-bowthruster, vessel? Over 40-knots
sustained with gusts over 50. It wasn't pretty, but we made it work.)

When conditions are fairly benign, it's easy to back into a slip with a single.
If your two deck mates can't fend off a 28-footer, there is no reason to expect
a magical difference with a 23 or 24-footer.
Unless there's a *major* screwup underway, one person is usually enough to make
minor manual adjustments on vessels of 35-40 feet.

With a single screw boat, you *must* take
the natural environment into account. Wind and current conditions will have a
huge effect on docking, as does what I call the "inside/outside" factor.

If the wind or current is up, my experience
says that the best approach is upwind, or upstream. You can bring out a few
more horses to make headway, but once you're "sailing" downwind or downstream
you are fairly well out of control.

The inside/outside factor: There seems to be a correlation between tight berths
and small fairways. Where you find one, you often encounter the other. When
making a turn from the fairway into a slip, try to approach from the angle that
will allow the side of the boat that needs to be next to the finger float to be
on the "outside" edge of the turn. IOW, turn to starboard to put the port side
against the pier, and turn to port to dock the starboard side. You want to have
fits? Just try to dock the "inside" edge. It can be done, but it's about three
times as difficult and why mess with it?

Then again there are times when the inside/outside factor and the wind or
current are contradictory. But not all that often...and if the wind or current
is extreme
that is the dominant variable IMO.

(I've pulled into guest moorage at marinas
and had twin screw boaters ask, "Why did you go past the slip and then do a 180
in the fairway and come at it from the other
side?" .....If you can solve the problem with
horsepower you don't learn to solve it with
strategy.)

The major difference between handling a single screw and twin screws is that
with a single you must plan a little more carefully and "think" your way to the
dock before you make your approach. Twin screws, you just sort of drive like a
bulldozer. :-)