The first two questions are matters of opinion, of course. Facts can help frame answers for the third question, though. I've looked at the performances of clubs promoted to the old Second/ new First Division for the sixteen seasons of the promotion playoffs era and have come up with some interesting stats on newly-promoted clubs prospects in the second tier. Here's what I've found:
* Of the 48 clubs promoted to the old Second/ new First Division
since the the playoffs system kicked in for the 1986-87 season, only
two gained automatic promotion. Sheffield United had finished second
in the old Third Division in 1988-89, winning automatic promotion and
returning to the old Second for the 1989-90 campaign. They proceeded
to finish second again and win their way back to the top flight. In
fact, they lost the championship to Leeds United on goal difference
alone. Manchester City won the Second Division playoffs in 1998-99
with their unforgettable triumph over Gillingham in the final, then
won automatic promotion to the Premiership by finishing second to
Division One in 1999-2000.
* Three other clubs have won promotion via the playoffs. In 1987-88,
Middlesbrough finished third in the old Second Division, then gained
a second straight promotion, beating Bradford City and Chelsea in the
playoffs. In 1990-91, Notts County landed in fourth place, then won
the playoffs by dispatching Middlesbrough and Brighton. Watford won
promotion via the playoffs in 1998-99. After finishing fifth, the
Hornets topped Birmingham and Bolton to go up.
* Another five clubs got as far as playoffs before falling short of
the promised land. Cambridge United took fifth in 1991-92 but lost
their semifinal to Leicester City. Reading finished second in 1994-
95 but had to go into the playoffs anyway. The Royals lost the final
to Bolton after getting past Tranmere in the semifinals. In 2000-01,
Preston North End came in fourth but lost the final to Bolton after
defeating Birmingham in the semis. The next year Millwall finished
fourth but lost to Birmingham in the semis. Last year Reading took
fourth but dropped their semifinal encounter with Wolves.
* In each of the last five seasons one of the three clubs promoted to
the First Division has got at least as far as the playoffs. The roll
call reads: Watford (1999), Manchester City (2000), Preston (2001),
Millwall (2002), and Reading (2003).
* In 10 of the last 16 seasons, one of the clubs promoted from the
third tier has got at least as far as the playoffs.
* Six of the 48 clubs have been relegated. Walsall finished 24th in
1988-89, Brentford 22nd in 1992-93, Burnley 22nd in 1994-95, Bristol
City 24th in 1998-99, Walsall 22nd in 1999-2000, and Brighton last
year.
* A total of 24, or precisely half of the 48 promoted clubs, have
finished in the top half of the table.
* Cardiff City are the fifth club to win promotion to the second
flight after finishing sixth in Division Two. Two of the first four
finished in the top half of the table the next season. Peterborough
finished 10th in 1992-93, Burnley 22nd in 1994-95, Bradford City 21st
in 1996-97, and Crewe 11th in 1997-98.
John Heyda