Jeeps are easy.
A positive attitude is a good thing. You have done your research and gathered some valuable info. Here are
some of the possible trouble areas.
1. The DB-ALL2 must be flashed with the correct firmware, currently it is 402.CHRYSLER2 v2.02.01.
2. Going D2D can cause all sorts of issues, but is supposed to work. The Python 533 is not a system I am familiar with but
here is a tip on a possible D2D problem with Directed starters : https://www.12voltdata.com/forum/viewtopic.php?f=131&t=8315
3. You will be using the Type 3 wiring diagram in the DB-ALL2 install guide. It does not show it clearly but your Jeep has one
Starter, one Ignition and two Accessory wires. No big deal. Just program the Python Flex relay to ACC2 and connect the H3
Pink/White wire to the Jeeps ACC2 wire.
4. According to the Type 3 diagram, the DB-ALL2 will control the Parking Lights via it's own direct connection to the Jeep.
This will probably be similar to the Bulldog method shown in this diagram :
https://diagrams.marktoonen.nl/DOWNLOADS/14301_GRAND-CHEROKEE_GRAND%20CHEROKEE%20PARKING%20LIGHT%20DIAGRAM.pdf
The DB-ALL2 will supply the correct resistor value.
5. The Tach signal via D2D could be an issue, so be prepared to hardwire that signal directly between the two modules.
Use a DMM, solder everything and drink plenty of water...
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Soldering is fun!
I've also found it helpful to set the Smart OEM Alarm Control on the DBALL2 to 'Disabled' or 'Normal' to help prevent issues with setting the factory alarm off during remote start.
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No question is stupid or not worth asking. You were once a noob, right? :)