Possibly Electrical Question?

I have a 1998 Jeep XJ with the 4.0 and I have an occasional (once every couple of weeks) anomaly that occurs. It has the tape deck only stereo in it (as opposed to the laser disk option) so I use a tape adapter for my phone that allows me to play playlists from my phone via the tape deck. Occasionally I will start the truck and it will refuse to recognize the adapter and eject it. Naturally I think the stereo is confused by the tape deck adapter so I turn it off as well as shut the truck down. Upon restarting it I notice it takes 7 at least cranks to get the engine going, sometimes I even need to tap the gas just a bit. (by tap the gas I mean hold it 1/4 of the way down until it starts and letting off the second its not cranking anymore)
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I have experimented with this during the majority of the time when It recognizes the tape and it has no issue starting back up. Anyone know why this would occur?

Sounds like a loss of fuel pressure.

It sounds to me like the ASD relay isn't working so when you shut down, it does not reset the IAC to the correct position.

How old is your battery.I had one that done the same thing because the battery was going south.It also would idle low after the start because the alternator was working to hard to charge the bad battery.Same with fuel pump is not getting enough volts because the starter was taking it all.Try a new or a good know battery and i bet your problems will go away.

Battery and fuel pump are new. This was a barn find I restored over the summer so its all new. I will have to do some research into the ASD relay along with the loss of pressure. Seems strange that it only happens on the rare occasion that I start my truck and the tape deck is acting up

I'd check the voltage while it is running and after it has sit over night. Sounds like it could be a low voltage issue.

I had iffy IAC issues twice, once was the battery and once was the alternator.

You might also want to test the voltage while cranking, anything below 9 volts or so and various electronics can act up

I did test the voltage while running recently. Definitely good, the voltage while sitting should be good as well because its a new battery as well as working alternator. But I will be looking into all of these things presidents day since I have it off