Going to look at a 98 Cherokee this weekend . The owner says it usually requires cycling the key twice for it to start. Almost sounds like the fuel pump loses its prime, but I'm not familiar with these fuel systems. Thoughts?
There is a one-way check valve inside the fuel pump to prevent drain-back that may be failing. It is serviced with the pump only AFAIK. Watching a fuel pressure gauge plummet after shutting off the engine would point to this as being the probable problem.