2001 Dodge Dakota Starting trouble. Sometimes

I would advise having your engine tested for problems using the Chrysler connector. I'm hoping the OBD connector showed only an emissions problem, but a evaporative problem can cause the exact trouble your experiencing because a type of vapor lock may be occuring under certain temperatures. The Chrysler scan may show up the sensor or other problem. Try loosening the gas cap, next time, before you think this long crank time may occur. All the emission systems have a direct effect on driveability and hard starting troubles. This was usually a fuel pump problem. No more.

Not on the first time. The first time I had a vapor lock problem was on a 75 Toyota p/up with CA. Emissions, it would get hot, and the pressure would raise putting the fuel system under positive pressure, of course this was low pressure carb. But electric pump. I changed a check valve. Now its more expensive. I've changed cannisters flooded, gas caps, sol. Switching valves, plugs, pump, all for this type of problem, and more.
Even though todays engines have more devices to handle fuel vapors, a failure in any part that is used for storing these vapors could cause this. The gas tank is the main source of vapors, and the fuel pump can be easily affected. I never saw too many that would cause a terrible start on a 50 psi system, but if its only hot, it could be this, there is a pump, valves, hoses and a gas cap that could be affecting your starting. See if before you start it, releasing the gas cap lets air out, this is one way, sometimes a suction is heard also. Usually long crank times are not too much temperature related but more consistant. So you may have an intermittant fuel pressure problem. But was ok when your mechanic tested it. Whatever the reason he told you that was causing his concern may be the clue. Glad to help. Also the charcoal cannister(used for storing these fuel vapors) is only purged back into your engine when its hot, the temp sensor controlling this or flooded cannister may be causing vapors to enter into your intake at the wrong time, you need to check Chryslers codes with their cable. Good luck out there. K?

Yes, it is possible, especially on a 2001. That is why a scan is necessary, it could even be the plugs that are unable to restart because of any number of rich fuel, or even lean fuel problems. The sensors that signal the engine computer could cause this. A fuel pump is another problem on the Dakota, so I would see if any fault codes are present, with a DRBIII(R), its pricey I know, but this is the way its done, its a very expensive test and scanner, but it helps find some problems other scanners miss. If you would like to check it yourself, a fuel pressure tester is necessary and they have a nice one at the store, its good for many uses too. You could connect it, and make sure your holding pressure ok, after you turn the engine off, if its too low, turning the key on repeatedly will help on a restart, ok. You need to check this as it happens with no fault codes, you could disconnect the vapor cannister purge hose on the intake it goes to the front cannister, if ok, you have found out that it is releasing fuel in the engine at the wrong timje.