First off let me just say, I'm an experienced auto tech, but have never laid hands on any Chrysler performance vehicles, or Durangos. I get very few Chrysler products in here aside from Rams, so I'm not 100% up on exactly how things work on that particular model. I can only tell you what I've seen based on experience. I do a TON of GM products. On the GM Silverado trucks, the fan comes on at a very low speed when the A/C is turned on ... USUALLY. On a cooler morning where you're trying to lower the humidity levels, it might not come on until a few minutes later. It comes on very low at first - sometimes you can barely hear it.
That said, on the Durango models I'm not sure what needs to be removed to access the condenser. It could range from just removing the top plate so you can look down inside, to having to remove most of the front clip / grille / bumper assembly.
The charts are normally accurate - just look at a few to be sure you're getting a good one (Not something someone made up on their desktop). I normally don't charge by looking at pressures solely. I charge by weight with a scale, and feel lines by hand, and have a thermometer in one of the center vents. A combination of this and experience tells me when it's charged good, with a little extra to be stored in the accumulator in case of a small leak. But, your static pressure vs. temperature can tell you if you've got air contamination, wrong refrigerant, etc..
Usually leaves, grass, pine needles, and that kind of debris are what I find the most between the condenser and radiator. Plastic bags are rare, but are always a possibility. Gauges will tell you exactly what is going on, sometimes. If your high side is climbing too high, that's also a dead ringer for a condenser airflow issue. If you hose the condenser down and the high side drops like a rock, bingo.
From what you describe I'd wager that system is not an orifice tube system, where the clutch cycles constantly based on pressures / demand. You more than likely have a TXV system (Thermal expansion valve) where the valve regulates refrigerant flow, while the compressor runs continuously. In this case, clutch issues are more rare than on an orifice tube system, but that's still always a possibility. You could also have a variable displacement compressor where the compressor itself changes output based on demands. Things can get a bit complicated for a DIY'er in that case. On many newer models like this, there's an evaporator sensor that can fail and cause issues, too, like low output of a variable displacement compressor.
Another thing to throw a wrench in the mix is the fact that most '18-up Chrysler products have a secure gateway, where you can't just plug a normal scan tool in. In some cases you have to disassemble the radio / display / HVAC assembly and plug into a module there with a special jumper in order to bypass the gateway. Otherwise you'll have extremely limited access to scan data. Sometimes that module is right under the dash, so it's easy. Other times you'll have to do some labor to reach it. You really need scan data on something this new to aid in troubleshooting. You need to watch pressures on the tool to see if they jive with what you're seeing on the gauges. Sometimes just a faulty pressure sensor can cause all these issues. If you watch a sensor jumping all around pressure wise, or occasionally hitting 0 PSI, then that sensor is more than likely dying. You'll also see a parameter in live data that says, "A/C inhibit" or something to that effect. If it says, "True" next to that, there's a problem electronically that's keeping the A/C off either permanently or intermittently. Sometimes a quick scan of the data will reveal what is inhibiting A/C operation. If a high pressure sensor is reading 600 PSI, that will kick it off for safety reasons, even if that data is false due to a failed sensor or a wiring, or connection issue.
There are many other variables when it comes to refrigerant, but if you're the 1st owner and you're sure nobody has been in that system, then those are less likely (Like contamination with the wrong refrigerant, air or moisture in the system, etc.).
I've never worked with the new YF refrigerant, but with most refrigerants, normally the low side will be around 20-40 psi depending on your ambient temperature, and the high can be anywhere from 120 psi (On the very low end) to 275 psi or higher. I like to see the high side around 150 psi most of the time, but this is with 134a or R12. With R12 it can be much lower.