Here's the thing: Virtually all of the owner/driver teams of the mid 90s were failures. Kulwicki's team won a title based on consistency and an almost freakish number of poles (6 in 29 races) - and as soon as Alan Passed, the 7 team absolutely plummeted under Geoff(rey) Bodine.
Darrell Waltrip: Had some initial successes in 1991-92, however, the bloom fell off the rose rather quickly after that. By Waltrip's admission he "thought more like a driver than an owner", and the team had more top 5s in it's first two years in operation than it's last five and a half, combined. The 17 team in particular seemed to hit a wall after Chevrolet changed from the Lumina back to the Monte Carlo in '95. And although Darrell might have lost a half-step from his 1980s form, his 1998 run with DEI proved VERY well that ole DW could still drive.
Ricky Rudd? Never burned through the racing world as an owner-driver, but probably the most consistently successful of the bunch. Good for a consistent 1-2 wins per year, usually through pure grit and determination (1998 @ Martinsville, anyone?). Still, the first three seasons after Rudd jumped to Robert Yates Racing absolutely dwarf his years as an owner-driver. His 14 Top 5's in 2011 was his best number in that category since 1981, and his highest points finish since 1991.
Elliott's success/lack thereof during his run as an owner-driver mimics that of Waltrip post-1993, although with less fall-off. His runs in the Thunderbird era (1995-97) were strong, if winless - while the changeover to the Taurus seemed to cause the team issues as the numbers fall off after that. And as with DW's DEI rebound, the changeover to Evernham/Dodge was a shot in the arm to Elliott - his stats returned to almost exactly where they were for most of his run with Junior Johnson, despite Elliott being 10 years older and with a brand new team.
Virtually every single flirtation with owner-operation in the 90s was a disaster. Elliott did the best he could with the resources he had, it was just an experiment that repeatedly proved itself not worth the investment.