The 97-98 Rockets featured:
Hakeem Olajuwon (35), Kevin Willis (35), Clyde Drexler (35) and Charles Barkley (34).
What would have happened if Drexler hadn't retired, Willis was retained and Pippen still came on board the next season and meshed with the team?
The 98-99 Rockets had some youth added to the team in the form of Michael Dickerson, Othella Harrington and Cuttino Mobley. The following season the team added Steve Francis.
How would the Rockets have faired if for the 98-99 season their team was:
CT: Olajuwon (36)/ Willis (36)
PF: Barkley (35)/ Othella Harrington
SF: Pippen (33)/ Sam Mack
SG: Drexler (36)/ Michael Dickerson
PG: Mobley/ Brent Price
Remember, Drexler was still producing good numbers and playing very well in his final season. Barkley still looked like an all-star, too. Olajuwon was starting to decline, but he was still better than most centers in the league not named Robinson, Duncan, Mourning or O'Neal.
I could see the above team getting to the conference finals, I don't know how they'd deal with the Lakers though.
How would the Rockets have faired for the 1999-2000 season:
CT: Olajuwon (37)/ Willis (37)
PF: Barkley (36)/ Kenn Thomas
SF: Pippen (34)/ Shandon Anderson
SG: Drexler (37)/ Cuttino Mobley
PG: Steve Francis/ Moochie Norris
I think at this stage the team would be too old in the front court to compete. Maybe a second round exit, and that's if Olajuwon, Drexler, Pippen and Barkley were healthy for the entire season.